Thermal stability, decomposition paths, and Ph/Ph exchange reactions of [(Ph3P)2Pd(Ph)X] (X = I, Br, Cl, F, and HF2)

Organometallics

Volumn 19, Issue 10, 2000, Pages 1888-1900

  Grushin, Vladimir V ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000682918     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0001265     Document Type: Article

References (121)

1. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
2. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
3. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
4. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
5. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
6. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
7. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
8. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
9. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
10. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
11. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
12. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
13. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
14. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
15. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
16. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
17. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
18. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
19. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
20. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
21. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
22. For selected recent reviews and monographs, see: (a) Negishi, E.-I. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; p 213. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Grushin, V. V.; Alper, H. Topics Organomet. Chem. 1999, 3, 193. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263. (e) Herrmann, W. A.; Reisinger, C.-P. In Aqueous-Phase Organometallic Catalysis; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998; p 383. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998; Org. React. 1997, 50, 1. (g) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852; Angew. Chem., Int. Ed. 1998, 37, 2046; Curr. Org. Chem. 1997, 1, 287; Synlett 1997, 329. (h) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167. (i) Browning, A. W.; Greeves, N. In Transition Metals in Organic Synthesis; Gibson, S. E., Ed.; Oxford University Press: Oxford, 1997; p 35. (j) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: London, 1997. (k) Stephenson, G. R. In Advances in Asymmetric Synthesis; Stephenson, G. R., Ed.; 1996; p 275. (l) Percec, V.; Hill, H. H. ACS Symp. Ser. 1996, 624, 2. (m) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (n) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (o) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2. (p) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589. (q) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 129.
23. 2b This decomposition path is obviously impossible for Pd aryls.
24. (b) Kawataka, F.; Kayaki, Y.; Shimizu, I.; Yamamoto, A. Organometallics 1994, 13, 3517.
25. Kong, K.-C.; Cheng, C.-H. J. Am. Chem. Soc. 1991, 113, 6313.
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27. (a) Segelstein, B. E.; Butler, T. W.; Chenard, B. L. J. Org. Chem. 1995, 60, 12.
28. (b) Hartwig and co-workers observed similar aryl-aryl exchange reactions when studying C-S reductive elimination from [LPd(Ar)SR], where L = bidentate phenylphosphine, e.g., dppe. See: Baranano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. Mann, G.; Baranano, D.; Hartwig, J. F.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1998, 120, 9205.
29. (b) Hartwig and co-workers observed similar aryl-aryl exchange reactions when studying C-S reductive elimination from [LPd(Ar)SR], where L = bidentate phenylphosphine, e.g., dppe. See: Baranano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937. Mann, G.; Baranano, D.; Hartwig, J. F.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1998, 120, 9205.
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33. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Beller, M.; Fischer, H. J. Organomet. Chem. 1995, 491, C1; J. Mol. Catal. A: Chem. 1995, 103, 133. O'Keefe, D. F.; Dannok, M C.; Marcuccio, S. M. Tetrahedron Lett. 1992, 33, 6679. Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695.
34. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Beller, M.; Fischer, H. J. Organomet. Chem. 1995, 491, C1; J. Mol. Catal. A: Chem. 1995, 103, 133. O'Keefe, D. F.; Dannok, M C.; Marcuccio, S. M. Tetrahedron Lett. 1992, 33, 6679. Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695.
35. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Beller, M.; Fischer, H. J. Organomet. Chem. 1995, 491, C1; J. Mol. Catal. A: Chem. 1995, 103, 133. O'Keefe, D. F.; Dannok, M C.; Marcuccio, S. M. Tetrahedron Lett. 1992, 33, 6679. Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695.
36. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Beller, M.; Fischer, H. J. Organomet. Chem. 1995, 491, C1; J. Mol. Catal. A: Chem. 1995, 103, 133. O'Keefe, D. F.; Dannok, M C.; Marcuccio, S. M. Tetrahedron Lett. 1992, 33, 6679. Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695.
37. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Beller, M.; Fischer, H. J. Organomet. Chem. 1995, 491, C1; J. Mol. Catal. A: Chem. 1995, 103, 133. O'Keefe, D. F.; Dannok, M C.; Marcuccio, S. M. Tetrahedron Lett. 1992, 33, 6679. Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695.
38. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Beller, M.; Fischer, H. J. Organomet. Chem. 1995, 491, C1; J. Mol. Catal. A: Chem. 1995, 103, 133. O'Keefe, D. F.; Dannok, M C.; Marcuccio, S. M. Tetrahedron Lett. 1992, 33, 6679. Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695.
39. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Beller, M.; Fischer, H. J. Organomet. Chem. 1995, 491, C1; J. Mol. Catal. A: Chem. 1995, 103, 133. O'Keefe, D. F.; Dannok, M C.; Marcuccio, S. M. Tetrahedron Lett. 1992, 33, 6679. Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695.
40. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Beller, M.; Fischer, H. J. Organomet. Chem. 1995, 491, C1; J. Mol. Catal. A: Chem. 1995, 103, 133. O'Keefe, D. F.; Dannok, M C.; Marcuccio, S. M. Tetrahedron Lett. 1992, 33, 6679. Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695.
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43. (b) Vicente, J.; Areas, A.; Bautista, D.; Tiripicchio, A.; Tiripicchio-Camellini, M. New J. Chem. 1996, 20, 345.
44. (c) Vicente, J.; Areas, A.; Bautista, D.; Jones, P. G. Organometallics 1997, 16, 2127.
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48. 6
49. 2Pd(Ar)I].
50. Fitton, P.; Rick, E. A. J. Organomet. Chem. 1971, 28, 287.
51. Flemming, J. P.; Pilon M. C.; Borbulevitch O. Ya.; Antipin M. Yu.; Grushin, V. V. Inorg. Chim. Acta 1998, 280, 87.
52. 2.
53. Amatore, C. A.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605.
54. - are all moderately soluble in benzene at 75 °C (5-10 mg/mL).
55. Reductive elimination reactions are often facilitated by ligand predissociation. See: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; p 322. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 2nd ed.; John Wiley and Sons: New York, 1994; p 151. Spessard, G. O.; Miessler, G. L. Organometallic Chemistry; Prentice Hall: Upper Saddle River, NJ, 1996; p 178.
56. Reductive elimination reactions are often facilitated by ligand predissociation. See: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; p 322. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 2nd ed.; John Wiley and Sons: New York, 1994; p 151. Spessard, G. O.; Miessler, G. L. Organometallic Chemistry; Prentice Hall: Upper Saddle River, NJ, 1996; p 178.
57. Reductive elimination reactions are often facilitated by ligand predissociation. See: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; p 322. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 2nd ed.; John Wiley and Sons: New York, 1994; p 151. Spessard, G. O.; Miessler, G. L. Organometallic Chemistry; Prentice Hall: Upper Saddle River, NJ, 1996; p 178.
58. 19c
59. (b) Kayaki, Y.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn 1997, 70, 1135.
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