An efficient palladium-catalyzed synthesis of unsymmetrical diaryl sulfones from aryl bromides/triflates and arenesulfinates

Synlett

Volumn , Issue 3, 2003, Pages 361-364

  Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Goggiamani, Antonella ^a   Parisi, Luca M ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Arenesulfinates; Catalysis; Coupling; Palladium; Sulfones

Indexed keywords

AMMONIUM DERIVATIVE; BROMINE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; ELECTRON; SYNTHESIS;

EID: 0037288966     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37117     Document Type: Article

References (75)

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32. 2 bonds, see: (a) Herd, O.; Hessler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69. (b) Herd, O.; Hessler, A.; Hingst, M.; Machnitzki, P.; Tepper, M.; Stelzer, O. Cat. Today 1998, 42, 413. (c) Machnitzki, P.; Nickel, T.; Stelzer, O.; Landgrafe, C. Eur. J. Inorg. Chem. 1998, 1029. (d) Kraatz, H.-B.; Pletsch, A. Tetrahedron: Asymmetry 2000, 11, 1617. (e) Machnitzki, P.; Tepper, M.; Wenz, K.; Stelzer, O.; Herdtweck, E. J. Organomet. Chem. 2000, 602, 158. (f) Hessler, A.; Kottsieper, K. W.; Schenk, S.; Tepper, M.; Stelzer, O. Z. Naturforsch. B 2001, 56, 347. (g) Brauer, D. J.; Hingst, M.; Kottsieper, K. W.; Liek, C.; Nickel, T.; Tepper, M.; Stelzer, O.; Sheldrick, W. S. J. Organomet. Chem. 2002, 645, 14.
33. 2 bonds, see: (a) Herd, O.; Hessler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69. (b) Herd, O.; Hessler, A.; Hingst, M.; Machnitzki, P.; Tepper, M.; Stelzer, O. Cat. Today 1998, 42, 413. (c) Machnitzki, P.; Nickel, T.; Stelzer, O.; Landgrafe, C. Eur. J. Inorg. Chem. 1998, 1029. (d) Kraatz, H.-B.; Pletsch, A. Tetrahedron: Asymmetry 2000, 11, 1617. (e) Machnitzki, P.; Tepper, M.; Wenz, K.; Stelzer, O.; Herdtweck, E. J. Organomet. Chem. 2000, 602, 158. (f) Hessler, A.; Kottsieper, K. W.; Schenk, S.; Tepper, M.; Stelzer, O. Z. Naturforsch. B 2001, 56, 347. (g) Brauer, D. J.; Hingst, M.; Kottsieper, K. W.; Liek, C.; Nickel, T.; Tepper, M.; Stelzer, O.; Sheldrick, W. S. J. Organomet. Chem. 2002, 645, 14.
34. 2 bonds, see: (a) Herd, O.; Hessler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69. (b) Herd, O.; Hessler, A.; Hingst, M.; Machnitzki, P.; Tepper, M.; Stelzer, O. Cat. Today 1998, 42, 413. (c) Machnitzki, P.; Nickel, T.; Stelzer, O.; Landgrafe, C. Eur. J. Inorg. Chem. 1998, 1029. (d) Kraatz, H.-B.; Pletsch, A. Tetrahedron: Asymmetry 2000, 11, 1617. (e) Machnitzki, P.; Tepper, M.; Wenz, K.; Stelzer, O.; Herdtweck, E. J. Organomet. Chem. 2000, 602, 158. (f) Hessler, A.; Kottsieper, K. W.; Schenk, S.; Tepper, M.; Stelzer, O. Z. Naturforsch. B 2001, 56, 347. (g) Brauer, D. J.; Hingst, M.; Kottsieper, K. W.; Liek, C.; Nickel, T.; Tepper, M.; Stelzer, O.; Sheldrick, W. S. J. Organomet. Chem. 2002, 645, 14.
35. 2 bonds, see: (a) Herd, O.; Hessler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69. (b) Herd, O.; Hessler, A.; Hingst, M.; Machnitzki, P.; Tepper, M.; Stelzer, O. Cat. Today 1998, 42, 413. (c) Machnitzki, P.; Nickel, T.; Stelzer, O.; Landgrafe, C. Eur. J. Inorg. Chem. 1998, 1029. (d) Kraatz, H.-B.; Pletsch, A. Tetrahedron: Asymmetry 2000, 11, 1617. (e) Machnitzki, P.; Tepper, M.; Wenz, K.; Stelzer, O.; Herdtweck, E. J. Organomet. Chem. 2000, 602, 158. (f) Hessler, A.; Kottsieper, K. W.; Schenk, S.; Tepper, M.; Stelzer, O. Z. Naturforsch. B 2001, 56, 347. (g) Brauer, D. J.; Hingst, M.; Kottsieper, K. W.; Liek, C.; Nickel, T.; Tepper, M.; Stelzer, O.; Sheldrick, W. S. J. Organomet. Chem. 2002, 645, 14.
36. 2 bonds, see: (a) Herd, O.; Hessler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69. (b) Herd, O.; Hessler, A.; Hingst, M.; Machnitzki, P.; Tepper, M.; Stelzer, O. Cat. Today 1998, 42, 413. (c) Machnitzki, P.; Nickel, T.; Stelzer, O.; Landgrafe, C. Eur. J. Inorg. Chem. 1998, 1029. (d) Kraatz, H.-B.; Pletsch, A. Tetrahedron: Asymmetry 2000, 11, 1617. (e) Machnitzki, P.; Tepper, M.; Wenz, K.; Stelzer, O.; Herdtweck, E. J. Organomet. Chem. 2000, 602, 158. (f) Hessler, A.; Kottsieper, K. W.; Schenk, S.; Tepper, M.; Stelzer, O. Z. Naturforsch. B 2001, 56, 347. (g) Brauer, D. J.; Hingst, M.; Kottsieper, K. W.; Liek, C.; Nickel, T.; Tepper, M.; Stelzer, O.; Sheldrick, W. S. J. Organomet. Chem. 2002, 645, 14.
37. 11c
38. 11c
39. 11c
40. 11c
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47. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
48. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
49. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
50. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
51. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
52. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
53. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
54. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
55. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
56. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
57. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
58. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
59. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
60. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
61. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
62. For the influence of halide additives on Pd(0)-catalyzed reactions, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Scott, J. W.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. (c) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813. (d) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629. (e) Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry; VCH: Weinheim, 1992, 254-272. (f) Jeffery, T.; Gallang, J. C. Tetrahedron Lett. 1994, 35, 4103. (g) Herrmann, W. H.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. (h) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52. 10225. (i) Jeffery, T. Tetrahedron 1996, 52, 10113. (j) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441. (k) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991. (l) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551. (m) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314; and the references therein. (n) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (o) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 2000, 4099. (p) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometaltics 2001, 20, 3724. (q) Larock, R. C.; Reddy, C. K. J. Org. Chem. 2002, 67, 2027.
63. For the influence of halide additives on divalent palladiumcatalyzed reactions, see: (a) Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393. (b) Bäckvall, J. E.; Äkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411. (c) Simone, D. O.; Kennelly, T.; Brungard, N. L.; Farrauto, R. J. Appl. Catal. 1991, 70, 87. (d) Francis, J. W.; Henry, P. M. J. Mol. Catal. 1995, 99, 77. (e) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 797. (f) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 904. (g) Widenhoefer, R. A.; Buchwald, S. L. Organometalllics 1996, 15, 2755. (h) Bäckvall, J. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 339-385.
64. For the influence of halide additives on divalent palladiumcatalyzed reactions, see: (a) Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393. (b) Bäckvall, J. E.; Äkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411. (c) Simone, D. O.; Kennelly, T.; Brungard, N. L.; Farrauto, R. J. Appl. Catal. 1991, 70, 87. (d) Francis, J. W.; Henry, P. M. J. Mol. Catal. 1995, 99, 77. (e) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 797. (f) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 904. (g) Widenhoefer, R. A.; Buchwald, S. L. Organometalllics 1996, 15, 2755. (h) Bäckvall, J. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 339-385.
65. For the influence of halide additives on divalent palladiumcatalyzed reactions, see: (a) Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393. (b) Bäckvall, J. E.; Äkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411. (c) Simone, D. O.; Kennelly, T.; Brungard, N. L.; Farrauto, R. J. Appl. Catal. 1991, 70, 87. (d) Francis, J. W.; Henry, P. M. J. Mol. Catal. 1995, 99, 77. (e) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 797. (f) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 904. (g) Widenhoefer, R. A.; Buchwald, S. L. Organometalllics 1996, 15, 2755. (h) Bäckvall, J. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 339-385.
66. For the influence of halide additives on divalent palladiumcatalyzed reactions, see: (a) Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393. (b) Bäckvall, J. E.; Äkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411. (c) Simone, D. O.; Kennelly, T.; Brungard, N. L.; Farrauto, R. J. Appl. Catal. 1991, 70, 87. (d) Francis, J. W.; Henry, P. M. J. Mol. Catal. 1995, 99, 77. (e) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 797. (f) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 904. (g) Widenhoefer, R. A.; Buchwald, S. L. Organometalllics 1996, 15, 2755. (h) Bäckvall, J. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 339-385.
67. For the influence of halide additives on divalent palladiumcatalyzed reactions, see: (a) Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393. (b) Bäckvall, J. E.; Äkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411. (c) Simone, D. O.; Kennelly, T.; Brungard, N. L.; Farrauto, R. J. Appl. Catal. 1991, 70, 87. (d) Francis, J. W.; Henry, P. M. J. Mol. Catal. 1995, 99, 77. (e) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 797. (f) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 904. (g) Widenhoefer, R. A.; Buchwald, S. L. Organometalllics 1996, 15, 2755. (h) Bäckvall, J. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 339-385.
68. For the influence of halide additives on divalent palladiumcatalyzed reactions, see: (a) Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393. (b) Bäckvall, J. E.; Äkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411. (c) Simone, D. O.; Kennelly, T.; Brungard, N. L.; Farrauto, R. J. Appl. Catal. 1991, 70, 87. (d) Francis, J. W.; Henry, P. M. J. Mol. Catal. 1995, 99, 77. (e) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 797. (f) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 904. (g) Widenhoefer, R. A.; Buchwald, S. L. Organometalllics 1996, 15, 2755. (h) Bäckvall, J. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 339-385.
69. For the influence of halide additives on divalent palladiumcatalyzed reactions, see: (a) Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393. (b) Bäckvall, J. E.; Äkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411. (c) Simone, D. O.; Kennelly, T.; Brungard, N. L.; Farrauto, R. J. Appl. Catal. 1991, 70, 87. (d) Francis, J. W.; Henry, P. M. J. Mol. Catal. 1995, 99, 77. (e) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 797. (f) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 904. (g) Widenhoefer, R. A.; Buchwald, S. L. Organometalllics 1996, 15, 2755. (h) Bäckvall, J. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 339-385.
70. For the influence of halide additives on divalent palladiumcatalyzed reactions, see: (a) Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393. (b) Bäckvall, J. E.; Äkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411. (c) Simone, D. O.; Kennelly, T.; Brungard, N. L.; Farrauto, R. J. Appl. Catal. 1991, 70, 87. (d) Francis, J. W.; Henry, P. M. J. Mol. Catal. 1995, 99, 77. (e) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 797. (f) Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: New York, 1995, 904. (g) Widenhoefer, R. A.; Buchwald, S. L. Organometalllics 1996, 15, 2755. (h) Bäckvall, J. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 339-385.
71. 10d (b) Yin, J.; Buchwald, L. S. Org. Lett. 2000, 2, 1101. (c) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539. (d) Rutherford, J. F.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc., article as soon as possible.
72. 10d (b) Yin, J.; Buchwald, L. S. Org. Lett. 2000, 2, 1101. (c) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539. (d) Rutherford, J. F.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc., article as soon as possible.
73. 10d (b) Yin, J.; Buchwald, L. S. Org. Lett. 2000, 2, 1101. (c) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539. (d) Rutherford, J. F.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc., article as soon as possible.
74. 10d (b) Yin, J.; Buchwald, L. S. Org. Lett. 2000, 2, 1101. (c) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539. (d) Rutherford, J. F.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc., article as soon as possible.
75. 4NCl were added (procedure A).