Palladium-catalyzed cascade reaction of α,β-unsaturated sulfones with aryl iodides

Chemistry - A European Journal

Volumn 9, Issue 7, 2003, Pages 1511-1520

  Mauleón, Pablo ^a   Núñez, Angel A ^a   Alonso, Inés ^a   Carretero, Juan C ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

C H activation; Domino reactions; Heck reaction; Palladium; Sulfones

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; ESTERS; PALLADIUM;

CASCADE REACTIONS;

UNSATURATED COMPOUNDS;

9,10 DIHYDROPHENANTHRENE DERIVATIVE; ALKENE; IODINE DERIVATIVE; PALLADACYCLE; PALLADIUM; PHENANTHRENE DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE; PHOSPHONIC ACID ESTER; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HECK REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0242684486     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390173     Document Type: Article

References (105)

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3. For recent reviews on the Heck reaction see: a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009; b) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314; c) A. de Meijere, F. E. Meyer in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 3; d) J. T Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 6; e) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427; f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371; g) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; h) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379. See, also: i) J. Tsuji, Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, Chichester, 1995.
4. For recent reviews on the Heck reaction see: a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009; b) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314; c) A. de Meijere, F. E. Meyer in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 3; d) J. T Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 6; e) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427; f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371; g) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; h) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379. See, also: i) J. Tsuji, Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, Chichester, 1995.
5. For recent reviews on the Heck reaction see: a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009; b) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314; c) A. de Meijere, F. E. Meyer in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 3; d) J. T Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 6; e) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427; f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371; g) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; h) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379. See, also: i) J. Tsuji, Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, Chichester, 1995.
6. For recent reviews on the Heck reaction see: a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009; b) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314; c) A. de Meijere, F. E. Meyer in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 3; d) J. T Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 6; e) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427; f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371; g) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; h) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379. See, also: i) J. Tsuji, Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, Chichester, 1995.
7. For recent reviews on the Heck reaction see: a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009; b) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314; c) A. de Meijere, F. E. Meyer in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 3; d) J. T Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 6; e) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427; f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371; g) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; h) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379. See, also: i) J. Tsuji, Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, Chichester, 1995.
8. For recent reviews on the Heck reaction see: a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009; b) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314; c) A. de Meijere, F. E. Meyer in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 3; d) J. T Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 6; e) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427; f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371; g) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; h) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379. See, also: i) J. Tsuji, Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, Chichester, 1995.
9. For recent reviews on the Heck reaction see: a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009; b) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314; c) A. de Meijere, F. E. Meyer in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 3; d) J. T Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 6; e) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427; f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371; g) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; h) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379. See, also: i) J. Tsuji, Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, Chichester, 1995.
10. For recent reviews on the Heck reaction see: a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009; b) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314; c) A. de Meijere, F. E. Meyer in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 3; d) J. T Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 6; e) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427; f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371; g) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; h) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379. See, also: i) J. Tsuji, Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, Chichester, 1995.
11. For recent reviews on the Heck reaction see: a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009; b) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314; c) A. de Meijere, F. E. Meyer in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 3; d) J. T Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 6; e) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427; f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371; g) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; h) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379. See, also: i) J. Tsuji, Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, Chichester, 1995.
12. For recent reviews on the Heck reaction see: a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009; b) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314; c) A. de Meijere, F. E. Meyer in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 3; d) J. T Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 6; e) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427; f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371; g) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; h) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379. See, also: i) J. Tsuji, Palladium Reagents and Catalysts; Innovations in Organic Synthesis, Wiley, Chichester, 1995.
13. For a review on the intramolecular Heck reaction, see: S. E. Gibson, R. J. Middleton, Contemp. Org. Synth. 1996, 3, 447.
14. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
15. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
16. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
17. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
18. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
19. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
20. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
21. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
22. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
23. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
24. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
25. For synthesis of trisubstituted olefins by Heck reaction of β-substituted α,β-unsaturated esters, nitriles, aldehydes, or ketones, see: a) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001,123, 6989; b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313; c) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107; d) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101; e) M. Moreno-Mañas, R. Pleixats, A. Roglans, Synlett 1997, 1157; f) S. Cacchi, P. G. Ciattini, E. Morena, P. Pace, Synlett 1996, 545; g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, P. Pace, Tetrahedron 1996, 52, 6983; h) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813; i) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1987, 28, 3039; j) L. S. Hegedus, P. J. Harrington, J. Org. Chem. 1984, 49, 2657; k) F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603; k) See also, ref. [31].
26. For the synthesis of trisubstituted acyclic α,β-unsaturated sulfoxides by Heck reaction, see: a) I. Alonso, J. C. Carretero, J. Org. Chem. 2001, 66, 4453; b) N. Díaz Buezo, O. García Mancheño, J. C. Carretero, Org. Lett. 2000, 2, 1451.
27. For the synthesis of trisubstituted acyclic α,β-unsaturated sulfoxides by Heck reaction, see: a) I. Alonso, J. C. Carretero, J. Org. Chem. 2001, 66, 4453; b) N. Díaz Buezo, O. García Mancheño, J. C. Carretero, Org. Lett. 2000, 2, 1451.
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60. For some recent reviews on palladium-mediated domino reactions, see: a) G. Poli, G. Giambastiani, A. Heumann, Tetrahedron 2000, 56, 5959; b) R. Grigg, V. Sridharan, J. Organomet. Chem. 1999, 576, 65; c) A. de Meijere, S. Bräse, J. Organomet. Chem. 1999, 576, 88.
61. For some recent reviews on palladium-mediated domino reactions, see: a) G. Poli, G. Giambastiani, A. Heumann, Tetrahedron 2000, 56, 5959; b) R. Grigg, V. Sridharan, J. Organomet. Chem. 1999, 576, 65; c) A. de Meijere, S. Bräse, J. Organomet. Chem. 1999, 576, 88.
62. For some recent reviews on palladium-mediated domino reactions, see: a) G. Poli, G. Giambastiani, A. Heumann, Tetrahedron 2000, 56, 5959; b) R. Grigg, V. Sridharan, J. Organomet. Chem. 1999, 576, 65; c) A. de Meijere, S. Bräse, J. Organomet. Chem. 1999, 576, 88.
63. Carbon-substituted palladacycle intermediates are also assumed to be involved in other types of palladium-catalyzed C-H activation processes. For reviews, see: a) G. Dyker, Angew. Chem. 1999, 111, 1808; Angew. Chem. Int. Ed. 1999, 38, 1698; b) G. Dyker, Chem. Ber./Recueil 1997, 130, 1567; c) M. Catellani, G. P. Chiusoli, Gazz. Chim. Ital. 1993, 123, 1. For the application of palladacycles in Heck type reactions, see: d) W. A. Herrmann, V. P. W. Bölm, C.-P. Reisinger, J. Organomet. Chem. 1999, 576, 23; e) see also ref. [11c].
64. Carbon-substituted palladacycle intermediates are also assumed to be involved in other types of palladium-catalyzed C-H activation processes. For reviews, see: a) G. Dyker, Angew. Chem. 1999, 111, 1808; Angew. Chem. Int. Ed. 1999, 38, 1698; b) G. Dyker, Chem. Ber./Recueil 1997, 130, 1567; c) M. Catellani, G. P. Chiusoli, Gazz. Chim. Ital. 1993, 123, 1. For the application of palladacycles in Heck type reactions, see: d) W. A. Herrmann, V. P. W. Bölm, C.-P. Reisinger, J. Organomet. Chem. 1999, 576, 23; e) see also ref. [11c].
65. Carbon-substituted palladacycle intermediates are also assumed to be involved in other types of palladium-catalyzed C-H activation processes. For reviews, see: a) G. Dyker, Angew. Chem. 1999, 111, 1808; Angew. Chem. Int. Ed. 1999, 38, 1698; b) G. Dyker, Chem. Ber./Recueil 1997, 130, 1567; c) M. Catellani, G. P. Chiusoli, Gazz. Chim. Ital. 1993, 123, 1. For the application of palladacycles in Heck type reactions, see: d) W. A. Herrmann, V. P. W. Bölm, C.-P. Reisinger, J. Organomet. Chem. 1999, 576, 23; e) see also ref. [11c].
66. Carbon-substituted palladacycle intermediates are also assumed to be involved in other types of palladium-catalyzed C-H activation processes. For reviews, see: a) G. Dyker, Angew. Chem. 1999, 111, 1808; Angew. Chem. Int. Ed. 1999, 38, 1698; b) G. Dyker, Chem. Ber./Recueil 1997, 130, 1567; c) M. Catellani, G. P. Chiusoli, Gazz. Chim. Ital. 1993, 123, 1. For the application of palladacycles in Heck type reactions, see: d) W. A. Herrmann, V. P. W. Bölm, C.-P. Reisinger, J. Organomet. Chem. 1999, 576, 23; e) see also ref. [11c].
67. Carbon-substituted palladacycle intermediates are also assumed to be involved in other types of palladium-catalyzed C-H activation processes. For reviews, see: a) G. Dyker, Angew. Chem. 1999, 111, 1808; Angew. Chem. Int. Ed. 1999, 38, 1698; b) G. Dyker, Chem. Ber./Recueil 1997, 130, 1567; c) M. Catellani, G. P. Chiusoli, Gazz. Chim. Ital. 1993, 123, 1. For the application of palladacycles in Heck type reactions, see: d) W. A. Herrmann, V. P. W. Bölm, C.-P. Reisinger, J. Organomet. Chem. 1999, 576, 23; e) see also ref. [11c].
68. Carbon-substituted palladacycle intermediates are also assumed to be involved in other types of palladium-catalyzed C-H activation processes. For reviews, see: a) G. Dyker, Angew. Chem. 1999, 111, 1808; Angew. Chem. Int. Ed. 1999, 38, 1698; b) G. Dyker, Chem. Ber./Recueil 1997, 130, 1567; c) M. Catellani, G. P. Chiusoli, Gazz. Chim. Ital. 1993, 123, 1. For the application of palladacycles in Heck type reactions, see: d) W. A. Herrmann, V. P. W. Bölm, C.-P. Reisinger, J. Organomet. Chem. 1999, 576, 23; e) see also ref. [11c].
69. The α,β-unsaturated sulfones 1 were readily prepared according to well-established procedures (by condensation of α-sulfonyl carbanions with aldehydes and further dehydration or by Wadsworth-Emmons olefination). For a review on synthesis of sulfones, see: a) N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon, Oxford, 1993. See also: b) G. H. Posner. D. J. Brunelle, J. Org. Chem. 1972, 37, 3547.
70. The α,β-unsaturated sulfones 1 were readily prepared according to well-established procedures (by condensation of α-sulfonyl carbanions with aldehydes and further dehydration or by Wadsworth-Emmons olefination). For a review on synthesis of sulfones, see: a) N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon, Oxford, 1993. See also: b) G. H. Posner. D. J. Brunelle, J. Org. Chem. 1972, 37, 3547.
71. Allyl sulfones tend to be more thermodynamically stable than vinyl sulfones (see, for example, ref. [13a], p. 39).
72. 2 (2 mol %) can be used in the domino arylation of 1a, both the conversion and the 4a:3a selectivity decreased significantly.
73. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-151679 (for 4a), CCDC-151680 (for 4e), and CCDC-181908 (for 4 h). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ. UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
74. We have noticed a slow isomerization of 3b to allyl phenyl sulfone even in a pure state at room temperature. In fact, to completely suppress the formation of allyl phenyl sulfone, 3b must be kept in the freezer once it has been purified by chromatography.
75. Dihydrophenanthrenes 4 can be routinely obtained with purities of 88-97% after flash chromatography. In most cases complete elimination of the minor Heck product was achieved by further recrystallization from diethyl ether.
76. 0 for 4e).
77. For the isolation of five-membered carbon substituted palladacycles, see, for instance: a) C. Fernández-Rivas, D. J. Cárdenas, B. Martín-Matute, A. Monge, E. Gutiérrez-Puebla, A. M. Echavarren, Organometallics 2001, 20, 2998, and references therein; b) M. Oesteich, P. R. Dennison, J. K. Kodanko, L. E. Overman, Angew. Chem. 2001, 113, 1485; Angew. Chem. Int. Ed. 2001, 40, 1439; c) C. Mateo, C. Fernández-Rivas, D. J. Cárdenas, A. M. Echavarren, Organometallics 1998, 17, 3661; d) C. Mateo, D. J. Cárdenas, C. Fernández-Rivas, A. M. Echavarren, Chem. Eur. J. 1996, 2, 1596; e) C.-H. Liu, C.-S. Li, C.-H Cheng, Organometallics 1994, 13, 18.
78. For the isolation of five-membered carbon substituted palladacycles, see, for instance: a) C. Fernández-Rivas, D. J. Cárdenas, B. Martín-Matute, A. Monge, E. Gutiérrez-Puebla, A. M. Echavarren, Organometallics 2001, 20, 2998, and references therein; b) M. Oesteich, P. R. Dennison, J. K. Kodanko, L. E. Overman, Angew. Chem. 2001, 113, 1485; Angew. Chem. Int. Ed. 2001, 40, 1439; c) C. Mateo, C. Fernández-Rivas, D. J. Cárdenas, A. M. Echavarren, Organometallics 1998, 17, 3661; d) C. Mateo, D. J. Cárdenas, C. Fernández-Rivas, A. M. Echavarren, Chem. Eur. J. 1996, 2, 1596; e) C.-H. Liu, C.-S. Li, C.-H Cheng, Organometallics 1994, 13, 18.
79. For the isolation of five-membered carbon substituted palladacycles, see, for instance: a) C. Fernández-Rivas, D. J. Cárdenas, B. Martín-Matute, A. Monge, E. Gutiérrez-Puebla, A. M. Echavarren, Organometallics 2001, 20, 2998, and references therein; b) M. Oesteich, P. R. Dennison, J. K. Kodanko, L. E. Overman, Angew. Chem. 2001, 113, 1485; Angew. Chem. Int. Ed. 2001, 40, 1439; c) C. Mateo, C. Fernández-Rivas, D. J. Cárdenas, A. M. Echavarren, Organometallics 1998, 17, 3661; d) C. Mateo, D. J. Cárdenas, C. Fernández-Rivas, A. M. Echavarren, Chem. Eur. J. 1996, 2, 1596; e) C.-H. Liu, C.-S. Li, C.-H Cheng, Organometallics 1994, 13, 18.
80. For the isolation of five-membered carbon substituted palladacycles, see, for instance: a) C. Fernández-Rivas, D. J. Cárdenas, B. Martín-Matute, A. Monge, E. Gutiérrez-Puebla, A. M. Echavarren, Organometallics 2001, 20, 2998, and references therein; b) M. Oesteich, P. R. Dennison, J. K. Kodanko, L. E. Overman, Angew. Chem. 2001, 113, 1485; Angew. Chem. Int. Ed. 2001, 40, 1439; c) C. Mateo, C. Fernández-Rivas, D. J. Cárdenas, A. M. Echavarren, Organometallics 1998, 17, 3661; d) C. Mateo, D. J. Cárdenas, C. Fernández-Rivas, A. M. Echavarren, Chem. Eur. J. 1996, 2, 1596; e) C.-H. Liu, C.-S. Li, C.-H Cheng, Organometallics 1994, 13, 18.
81. For the isolation of five-membered carbon substituted palladacycles, see, for instance: a) C. Fernández-Rivas, D. J. Cárdenas, B. Martín-Matute, A. Monge, E. Gutiérrez-Puebla, A. M. Echavarren, Organometallics 2001, 20, 2998, and references therein; b) M. Oesteich, P. R. Dennison, J. K. Kodanko, L. E. Overman, Angew. Chem. 2001, 113, 1485; Angew. Chem. Int. Ed. 2001, 40, 1439; c) C. Mateo, C. Fernández-Rivas, D. J. Cárdenas, A. M. Echavarren, Organometallics 1998, 17, 3661; d) C. Mateo, D. J. Cárdenas, C. Fernández-Rivas, A. M. Echavarren, Chem. Eur. J. 1996, 2, 1596; e) C.-H. Liu, C.-S. Li, C.-H Cheng, Organometallics 1994, 13, 18.
82. For the isolation of five-membered carbon substituted palladacycles, see, for instance: a) C. Fernández-Rivas, D. J. Cárdenas, B. Martín-Matute, A. Monge, E. Gutiérrez-Puebla, A. M. Echavarren, Organometallics 2001, 20, 2998, and references therein; b) M. Oesteich, P. R. Dennison, J. K. Kodanko, L. E. Overman, Angew. Chem. 2001, 113, 1485; Angew. Chem. Int. Ed. 2001, 40, 1439; c) C. Mateo, C. Fernández-Rivas, D. J. Cárdenas, A. M. Echavarren, Organometallics 1998, 17, 3661; d) C. Mateo, D. J. Cárdenas, C. Fernández-Rivas, A. M. Echavarren, Chem. Eur. J. 1996, 2, 1596; e) C.-H. Liu, C.-S. Li, C.-H Cheng, Organometallics 1994, 13, 18.
83. Review on organopalladium(iv) chemistry: A. J. Canty, Acc. Chem. Res. 1992, 25, 83.
84. IV five-membered palladacycles, see for instance: a) M. Catellani, G. P. Chiusoli, M. Costa, J. Organomet. Chem. 1995, 500, 69; b) G. Bocelli, M. Catellani, S. Ghelli, J. Organomet. Chem. 1993, 458, C12; c) M. Catellani, B. E. Mann, J. Organomet. Chem. 1990, 390, 251; d) see also reference [10]. For the isolation and X-ray structure of an arylpalladium(IV) five-membered palladacycle, see: e) J. M. Brunel, M.-H. Hirlemann, A. Heumann, G. Buono, Chem. Commun. 2000, 1869.
85. IV five-membered palladacycles, see for instance: a) M. Catellani, G. P. Chiusoli, M. Costa, J. Organomet. Chem. 1995, 500, 69; b) G. Bocelli, M. Catellani, S. Ghelli, J. Organomet. Chem. 1993, 458, C12; c) M. Catellani, B. E. Mann, J. Organomet. Chem. 1990, 390, 251; d) see also reference [10]. For the isolation and X-ray structure of an arylpalladium(IV) five-membered palladacycle, see: e) J. M. Brunel, M.-H. Hirlemann, A. Heumann, G. Buono, Chem. Commun. 2000, 1869.
86. IV five-membered palladacycles, see for instance: a) M. Catellani, G. P. Chiusoli, M. Costa, J. Organomet. Chem. 1995, 500, 69; b) G. Bocelli, M. Catellani, S. Ghelli, J. Organomet. Chem. 1993, 458, C12; c) M. Catellani, B. E. Mann, J. Organomet. Chem. 1990, 390, 251; d) see also reference [10]. For the isolation and X-ray structure of an arylpalladium(IV) five-membered palladacycle, see: e) J. M. Brunel, M.-H. Hirlemann, A. Heumann, G. Buono, Chem. Commun. 2000, 1869.
87. IV five-membered palladacycles, see for instance: a) M. Catellani, G. P. Chiusoli, M. Costa, J. Organomet. Chem. 1995, 500, 69; b) G. Bocelli, M. Catellani, S. Ghelli, J. Organomet. Chem. 1993, 458, C12; c) M. Catellani, B. E. Mann, J. Organomet. Chem. 1990, 390, 251; d) see also reference [10]. For the isolation and X-ray structure of an arylpalladium(IV) five-membered palladacycle, see: e) J. M. Brunel, M.-H. Hirlemann, A. Heumann, G. Buono, Chem. Commun. 2000, 1869.
88. IV five-membered palladacycles, see for instance: a) M. Catellani, G. P. Chiusoli, M. Costa, J. Organomet. Chem. 1995, 500, 69; b) G. Bocelli, M. Catellani, S. Ghelli, J. Organomet. Chem. 1993, 458, C12; c) M. Catellani, B. E. Mann, J. Organomet. Chem. 1990, 390, 251; d) see also reference [10]. For the isolation and X-ray structure of an arylpalladium(IV) five-membered palladacycle, see: e) J. M. Brunel, M.-H. Hirlemann, A. Heumann, G. Buono, Chem. Commun. 2000, 1869.
89. II complexes, see: G. Dyker, Chem. Ber 1994, 127, 739.
90. For the isolation of seven-membered palladacycles, see: A. S. K. Hashmi, A. R. Nass, J. W. Bats, M. Bolte, Angew. Chem. 1999, 111, 3565; Angew. Chem. Int. Ed. 1999, 38, 3370.
91. For the isolation of seven-membered palladacycles, see: A. S. K. Hashmi, A. R. Nass, J. W. Bats, M. Bolte, Angew. Chem. 1999, 111, 3565; Angew. Chem. Int. Ed. 1999, 38, 3370.
92. Unlike the reaction with p-iodotoluene, the reaction with o-iodotoluene and m-iodotoluene afforded complex mixtures of products.
93. 8).
94. 2, hv) and reductive cleavage of the C-I bond (58 % overall yield) following the procedure described in the literature for the preparation of cis-1e: a) G. L. Edwards, C. A. Muldoon, D. J. Sinclair, Tetrahedron 1996, 52, 7779; b) W. E. Truce, G. C Wolf, J. Org. Chem. 1971, 36, 1727.
95. 2, hv) and reductive cleavage of the C-I bond (58 % overall yield) following the procedure described in the literature for the preparation of cis-1e: a) G. L. Edwards, C. A. Muldoon, D. J. Sinclair, Tetrahedron 1996, 52, 7779; b) W. E. Truce, G. C Wolf, J. Org. Chem. 1971, 36, 1727.
96. II). For a recent reference, see: V. P. W. Böhm, W. A. Herrmann, Chem. Eur J. 2001, 7, 4191, and references therein.
97. 3.
98. The E stereochemistry of several trisubstituted olefins 3 and 25 was unequivocally established by NOESY experiments.
99. For a related coordination control in Heck reactions of 2-pyridyldimethylsilyl-substituted alkenes, see: a) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577; b) K. Itami, T. Nokami, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 5600; c) K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, J.-I Yoshida, J. Am. Chem. Soc. 2000, 122, 12013. For Pd-N coordinated complexes in Heck reaction of nitrogen-containing vinyl ethers, see: d) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2001, 123, 8217; e) M. Larhed, C. Andersson, A. Hallberg, Tetrahedron 1994, 50, 285; f) see also ref. [5].
100. For a related coordination control in Heck reactions of 2-pyridyldimethylsilyl-substituted alkenes, see: a) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577; b) K. Itami, T. Nokami, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 5600; c) K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, J.-I Yoshida, J. Am. Chem. Soc. 2000, 122, 12013. For Pd-N coordinated complexes in Heck reaction of nitrogen-containing vinyl ethers, see: d) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2001, 123, 8217; e) M. Larhed, C. Andersson, A. Hallberg, Tetrahedron 1994, 50, 285; f) see also ref. [5].
101. For a related coordination control in Heck reactions of 2-pyridyldimethylsilyl-substituted alkenes, see: a) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577; b) K. Itami, T. Nokami, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 5600; c) K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, J.-I Yoshida, J. Am. Chem. Soc. 2000, 122, 12013. For Pd-N coordinated complexes in Heck reaction of nitrogen-containing vinyl ethers, see: d) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2001, 123, 8217; e) M. Larhed, C. Andersson, A. Hallberg, Tetrahedron 1994, 50, 285; f) see also ref. [5].
102. For a related coordination control in Heck reactions of 2-pyridyldimethylsilyl-substituted alkenes, see: a) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577; b) K. Itami, T. Nokami, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 5600; c) K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, J.-I Yoshida, J. Am. Chem. Soc. 2000, 122, 12013. For Pd-N coordinated complexes in Heck reaction of nitrogen-containing vinyl ethers, see: d) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2001, 123, 8217; e) M. Larhed, C. Andersson, A. Hallberg, Tetrahedron 1994, 50, 285; f) see also ref. [5].
103. For a related coordination control in Heck reactions of 2-pyridyldimethylsilyl-substituted alkenes, see: a) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577; b) K. Itami, T. Nokami, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 5600; c) K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, J.-I Yoshida, J. Am. Chem. Soc. 2000, 122, 12013. For Pd-N coordinated complexes in Heck reaction of nitrogen-containing vinyl ethers, see: d) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2001, 123, 8217; e) M. Larhed, C. Andersson, A. Hallberg, Tetrahedron 1994, 50, 285; f) see also ref. [5].
104. For a related coordination control in Heck reactions of 2-pyridyldimethylsilyl-substituted alkenes, see: a) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577; b) K. Itami, T. Nokami, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 5600; c) K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, J.-I Yoshida, J. Am. Chem. Soc. 2000, 122, 12013. For Pd-N coordinated complexes in Heck reaction of nitrogen-containing vinyl ethers, see: d) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2001, 123, 8217; e) M. Larhed, C. Andersson, A. Hallberg, Tetrahedron 1994, 50, 285; f) see also ref. [5].
105. G. M. Sheldrick, University of Göttingen, Göttingen (Germany), 1998.