The tertiary sulfonamide as a latent directed-metalation group: Ni 0-catalyzed reductive cleavage and cross-coupling reactions of aryl sulfonamides with Grignard reagents

Angewandte Chemie - International Edition

Volumn 43, Issue 7, 2004, Pages 888-891

  Milburn, Robert R ^a   Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

Arenes; Cross coupling; Magnesium; Nickel; Sulfonamides

Indexed keywords

AMINATION; AROMATIC HYDROCARBONS; CATALYSTS; NICKEL COMPOUNDS; PRASEODYMIUM COMPOUNDS; SUBSTITUTION REACTIONS;

GRIGNARD REAGENTS; METALATION; TERARYL COMPOUNDS;

SULFONATION;

NICKEL; SULFONAMIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; GRIGNARD REACTION; METAL BINDING; REACTION ANALYSIS; REDUCTION KINETICS; SUBSTITUTION REACTION;

EID: 4544291000     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352633     Document Type: Article

References (51)

1. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
2. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
3. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
4. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
5. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
6. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
7. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
8. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
9. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
10. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
11. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
12. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
13. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
14. For a summary, see the special issue dedicated to the field: Eds.: K. Tamao, T. Hiyama, E.-i. Negishi, J. Organomet. Chem. 2002, 653; Stille coupling: I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551; Negishi coupling: A. O. King, E.-i. Negishi, F. J. Villani, A. Silveira, J. Org. Chem. 1978, 43, 358; I. Klement, M. Rottlander, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201; Hiyama coupling: Y. Hatanaka, T. Hiyama, Synlett 1991, 845; S. E. Denmark, T. F. Sweis, Acc. Chem. Res. 2002, 35, 835; Suzuki-Miyaura coupling: N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 867; S. Kotha, K. Lahiri, S. Kashinath, Tetrahedron 2002, 58, 9633; Corriu-Kumada-Tamao reaction: K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374; R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144; for a recent copper-catalyzed coupling of siloxanes, see: P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600; for the copper-catalyzed coupling of boronic acids, see: P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691; for iron-catalyzed coupling, see: A. Fürstner, A. Leitner, M. M. Menendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856, and references therein.
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31. See also: Annu. Rep. Med. Chem. 2002, 37, pp. 3, 4, 17, 46-48, 54-57, 66, 70, 72, 81, 87, 88, 91, 131, 135, 136, 139, 142, 242, 252; G. Bouchain, S. Leit, S. Frechette, E. A. Khalil, R. Lavoie, O. Moradei, S. H. Woo, M. Fournel, P. T. Yan, A. Lakita, M.-C. Trachy-Bourget, C. Beaulieu, Z. Li, M.-F. Robert, R. MacLeod, J. M. Besterman, D. Delorme, J. Med. Chem. 2003, 46, 820; E. Pomarnzcka, M. Gdaniec, Bioorg. Med. Chem. 2003, 11, 1259; M. Nakamura, M. Yamaguchi, O. Sakai, J. Inoue, Bioorg. Med. Chem. 2003, 11, 1371; N. Murugesan, Z. Gu, S. Spergel, M. Young, P. Chen, A. Mathur, L. Leith, M. Hermsmeier, E. C.-K. Liu, R. Zhang, E. Bird, T. Waldron, A. Marino, B. Koplowitz, W. G. Humphreys, S. Chong, R. A. Morrison, M. L. Webb, S. Moreland, N. Trippodo, J. C. Barrish, J. Med. Chem. 2003, 46, 125; Y. M. Choi-Sledeski, R. Kearney, G. Poli, H. Pauls, C. Gardner, Y. Gong, M. Becker, R. Davis, A. Spada, G. Liang, V. Chu, K. Brown, D. Collussi, R. Leadley, S. Rebello, P. Moxey, S. Morgan, R. Bentley, S. Lasiewshi, S. Maignan, J.-P. Guilloteau, V. Mikol, J. Med. Chem. 2003, 46, 681.
32. See also: Annu. Rep. Med. Chem. 2002, 37, pp. 3, 4, 17, 46-48, 54-57, 66, 70, 72, 81, 87, 88, 91, 131, 135, 136, 139, 142, 242, 252; G. Bouchain, S. Leit, S. Frechette, E. A. Khalil, R. Lavoie, O. Moradei, S. H. Woo, M. Fournel, P. T. Yan, A. Lakita, M.-C. Trachy-Bourget, C. Beaulieu, Z. Li, M.-F. Robert, R. MacLeod, J. M. Besterman, D. Delorme, J. Med. Chem. 2003, 46, 820; E. Pomarnzcka, M. Gdaniec, Bioorg. Med. Chem. 2003, 11, 1259; M. Nakamura, M. Yamaguchi, O. Sakai, J. Inoue, Bioorg. Med. Chem. 2003, 11, 1371; N. Murugesan, Z. Gu, S. Spergel, M. Young, P. Chen, A. Mathur, L. Leith, M. Hermsmeier, E. C.-K. Liu, R. Zhang, E. Bird, T. Waldron, A. Marino, B. Koplowitz, W. G. Humphreys, S. Chong, R. A. Morrison, M. L. Webb, S. Moreland, N. Trippodo, J. C. Barrish, J. Med. Chem. 2003, 46, 125; Y. M. Choi-Sledeski, R. Kearney, G. Poli, H. Pauls, C. Gardner, Y. Gong, M. Becker, R. Davis, A. Spada, G. Liang, V. Chu, K. Brown, D. Collussi, R. Leadley, S. Rebello, P. Moxey, S. Morgan, R. Bentley, S. Lasiewshi, S. Maignan, J.-P. Guilloteau, V. Mikol, J. Med. Chem. 2003, 46, 681.
33. See also: Annu. Rep. Med. Chem. 2002, 37, pp. 3, 4, 17, 46-48, 54-57, 66, 70, 72, 81, 87, 88, 91, 131, 135, 136, 139, 142, 242, 252; G. Bouchain, S. Leit, S. Frechette, E. A. Khalil, R. Lavoie, O. Moradei, S. H. Woo, M. Fournel, P. T. Yan, A. Lakita, M.-C. Trachy-Bourget, C. Beaulieu, Z. Li, M.-F. Robert, R. MacLeod, J. M. Besterman, D. Delorme, J. Med. Chem. 2003, 46, 820; E. Pomarnzcka, M. Gdaniec, Bioorg. Med. Chem. 2003, 11, 1259; M. Nakamura, M. Yamaguchi, O. Sakai, J. Inoue, Bioorg. Med. Chem. 2003, 11, 1371; N. Murugesan, Z. Gu, S. Spergel, M. Young, P. Chen, A. Mathur, L. Leith, M. Hermsmeier, E. C.-K. Liu, R. Zhang, E. Bird, T. Waldron, A. Marino, B. Koplowitz, W. G. Humphreys, S. Chong, R. A. Morrison, M. L. Webb, S. Moreland, N. Trippodo, J. C. Barrish, J. Med. Chem. 2003, 46, 125; Y. M. Choi-Sledeski, R. Kearney, G. Poli, H. Pauls, C. Gardner, Y. Gong, M. Becker, R. Davis, A. Spada, G. Liang, V. Chu, K. Brown, D. Collussi, R. Leadley, S. Rebello, P. Moxey, S. Morgan, R. Bentley, S. Lasiewshi, S. Maignan, J.-P. Guilloteau, V. Mikol, J. Med. Chem. 2003, 46, 681.
34. See also: Annu. Rep. Med. Chem. 2002, 37, pp. 3, 4, 17, 46-48, 54-57, 66, 70, 72, 81, 87, 88, 91, 131, 135, 136, 139, 142, 242, 252; G. Bouchain, S. Leit, S. Frechette, E. A. Khalil, R. Lavoie, O. Moradei, S. H. Woo, M. Fournel, P. T. Yan, A. Lakita, M.-C. Trachy-Bourget, C. Beaulieu, Z. Li, M.-F. Robert, R. MacLeod, J. M. Besterman, D. Delorme, J. Med. Chem. 2003, 46, 820; E. Pomarnzcka, M. Gdaniec, Bioorg. Med. Chem. 2003, 11, 1259; M. Nakamura, M. Yamaguchi, O. Sakai, J. Inoue, Bioorg. Med. Chem. 2003, 11, 1371; N. Murugesan, Z. Gu, S. Spergel, M. Young, P. Chen, A. Mathur, L. Leith, M. Hermsmeier, E. C.-K. Liu, R. Zhang, E. Bird, T. Waldron, A. Marino, B. Koplowitz, W. G. Humphreys, S. Chong, R. A. Morrison, M. L. Webb, S. Moreland, N. Trippodo, J. C. Barrish, J. Med. Chem. 2003, 46, 125; Y. M. Choi-Sledeski, R. Kearney, G. Poli, H. Pauls, C. Gardner, Y. Gong, M. Becker, R. Davis, A. Spada, G. Liang, V. Chu, K. Brown, D. Collussi, R. Leadley, S. Rebello, P. Moxey, S. Morgan, R. Bentley, S. Lasiewshi, S. Maignan, J.-P. Guilloteau, V. Mikol, J. Med. Chem. 2003, 46, 681.
35. See also: Annu. Rep. Med. Chem. 2002, 37, pp. 3, 4, 17, 46-48, 54-57, 66, 70, 72, 81, 87, 88, 91, 131, 135, 136, 139, 142, 242, 252; G. Bouchain, S. Leit, S. Frechette, E. A. Khalil, R. Lavoie, O. Moradei, S. H. Woo, M. Fournel, P. T. Yan, A. Lakita, M.-C. Trachy-Bourget, C. Beaulieu, Z. Li, M.-F. Robert, R. MacLeod, J. M. Besterman, D. Delorme, J. Med. Chem. 2003, 46, 820; E. Pomarnzcka, M. Gdaniec, Bioorg. Med. Chem. 2003, 11, 1259; M. Nakamura, M. Yamaguchi, O. Sakai, J. Inoue, Bioorg. Med. Chem. 2003, 11, 1371; N. Murugesan, Z. Gu, S. Spergel, M. Young, P. Chen, A. Mathur, L. Leith, M. Hermsmeier, E. C.-K. Liu, R. Zhang, E. Bird, T. Waldron, A. Marino, B. Koplowitz, W. G. Humphreys, S. Chong, R. A. Morrison, M. L. Webb, S. Moreland, N. Trippodo, J. C. Barrish, J. Med. Chem. 2003, 46, 125; Y. M. Choi-Sledeski, R. Kearney, G. Poli, H. Pauls, C. Gardner, Y. Gong, M. Becker, R. Davis, A. Spada, G. Liang, V. Chu, K. Brown, D. Collussi, R. Leadley, S. Rebello, P. Moxey, S. Morgan, R. Bentley, S. Lasiewshi, S. Maignan, J.-P. Guilloteau, V. Mikol, J. Med. Chem. 2003, 46, 681.
36. See also: Annu. Rep. Med. Chem. 2002, 37, pp. 3, 4, 17, 46-48, 54-57, 66, 70, 72, 81, 87, 88, 91, 131, 135, 136, 139, 142, 242, 252; G. Bouchain, S. Leit, S. Frechette, E. A. Khalil, R. Lavoie, O. Moradei, S. H. Woo, M. Fournel, P. T. Yan, A. Lakita, M.-C. Trachy-Bourget, C. Beaulieu, Z. Li, M.-F. Robert, R. MacLeod, J. M. Besterman, D. Delorme, J. Med. Chem. 2003, 46, 820; E. Pomarnzcka, M. Gdaniec, Bioorg. Med. Chem. 2003, 11, 1259; M. Nakamura, M. Yamaguchi, O. Sakai, J. Inoue, Bioorg. Med. Chem. 2003, 11, 1371; N. Murugesan, Z. Gu, S. Spergel, M. Young, P. Chen, A. Mathur, L. Leith, M. Hermsmeier, E. C.-K. Liu, R. Zhang, E. Bird, T. Waldron, A. Marino, B. Koplowitz, W. G. Humphreys, S. Chong, R. A. Morrison, M. L. Webb, S. Moreland, N. Trippodo, J. C. Barrish, J. Med. Chem. 2003, 46, 125; Y. M. Choi-Sledeski, R. Kearney, G. Poli, H. Pauls, C. Gardner, Y. Gong, M. Becker, R. Davis, A. Spada, G. Liang, V. Chu, K. Brown, D. Collussi, R. Leadley, S. Rebello, P. Moxey, S. Morgan, R. Bentley, S. Lasiewshi, S. Maignan, J.-P. Guilloteau, V. Mikol, J. Med. Chem. 2003, 46, 681.
37. 2] was found to be an effective catalyst. The control experiment without catalyst gave no reaction. Catalyst loadings of 1 mol % gave slightly lower yields. Use of THF and hexanes as solvents and the addition of phosphane ligands gave poor yields. The nature of the amine portion of the sulfonamide (e.g. sterically demanding or aromatic) had a negligible influence on the yield. Secondary amines were inert to the reaction conditions, possibly due to the insolubility of their magnesium salts.
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46. Recently, the conversion of 7i→15b (Table 3) was effected at room temperature in 54% yield in the presence of catalytic [CpNi(IMes)Cl]: C. D. Abernethy, A. H. Cowley, R. A. Jones, J. Organomet. Chem. 2000, 596, 3; R. R. Milburn, A. Pla, V. Snieckus, unpublished results (Mes = mesityl = 2,4,6-trimethylphenyl).
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