Anti-Markonikov reactions, 6. Rhodium-catalyzed amination of vinylpyridines: Hydroamination versus oxidative amination

European Journal of Inorganic Chemistry

Volumn , Issue 7, 1999, Pages 1121-1132

  Beller, Matthias ^a,b   Trauthwein, Harald ^b   Eichberger, Martin ^c   Breindl, Claudia ^b   Müller, Thomas E ^b  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c NONE

Author keywords

Aminations; Coordination chemistry; Hydroaminations; Oxidative aminations; Rhodium; Vinylpyridines

Indexed keywords

AMINES; COORDINATION REACTIONS; RHODIUM COMPOUNDS; X RAY DIFFRACTION ANALYSIS;

CATALYSE; CATIONICS; CO-ORDINATION CHEMISTRIES; HYDROAMINATIONS; OXIDATIVE AMINATION; REACTION CONDITIONS; RHODIUM COMPLEXES; RHODIUM-CATALYZED; SECONDARY AMINES; VINYLPYRIDINE;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

PYRIDINE DERIVATIVE; RHODIUM; RHODIUM COMPLEX;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 0032771364     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0682(199907)1999:7<1121::aid-ejic1121>3.0.co;2-8     Document Type: Article

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6. For a recent review see: T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675. [2a] D. R. Coulson (Du Pont), US 3.758.586, 1973; Chem. Abstr. 1973, 79, 125808g. [2b] D. R. Coulson, Tetrahedron Lett. 1971, 429. [2c] L. S. Hegedus, Angew. Chem. 1988, 100, 1147; Angew. Chem. Int. Ed. Engl 1988, 27, 1113. [2d] A. L. Casalnuovo, J. L. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738. [2e] D. Steinborn, B. Thies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333. [2f] M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108. [2g] D. Selent, D. Scharfenberg-Pfeiffer, G. Reck, R. Taube, J. Organomet. Chem. 1991, 415, 417. [2h] M. R. Gagné, C. L. Stern, T. J. Marks, J. Am Chem. Soc 1992, 114, 275. [2i] J.-J. Brunet, D. Neibecker, K. Philippot, Tetrahedron Lett. 1993, 34, 3877. [2j] R. C. Larock, T. R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584. [2k] Y. Li, T. J. Marks, J. Am. Chem. Soc 1996, 118, 707. [2l] Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295. [2m] Y. W. Li, T J. Marks, Organometallics 1996, 15, 10212. [2n] C. Hahn, J. Sieler, R. Taube, Chem. Ber. 1997, 130, 939. [2o] R. Dorta, P. Egli, F. Zürchner, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857. [2p] C. Hahn, A. Vitagliano, F. Giordano, R. Taube, Organometallics 1998, 17, 2060.
7. For a recent review see: T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675. [2a] D. R. Coulson (Du Pont), US 3.758.586, 1973; Chem. Abstr. 1973, 79, 125808g. [2b] D. R. Coulson, Tetrahedron Lett. 1971, 429. [2c] L. S. Hegedus, Angew. Chem. 1988, 100, 1147; Angew. Chem. Int. Ed. Engl 1988, 27, 1113. [2d] A. L. Casalnuovo, J. L. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738. [2e] D. Steinborn, B. Thies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333. [2f] M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108. [2g] D. Selent, D. Scharfenberg-Pfeiffer, G. Reck, R. Taube, J. Organomet. Chem. 1991, 415, 417. [2h] M. R. Gagné, C. L. Stern, T. J. Marks, J. Am Chem. Soc 1992, 114, 275. [2i] J.-J. Brunet, D. Neibecker, K. Philippot, Tetrahedron Lett. 1993, 34, 3877. [2j] R. C. Larock, T. R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584. [2k] Y. Li, T. J. Marks, J. Am. Chem. Soc 1996, 118, 707. [2l] Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295. [2m] Y. W. Li, T J. Marks, Organometallics 1996, 15, 10212. [2n] C. Hahn, J. Sieler, R. Taube, Chem. Ber. 1997, 130, 939. [2o] R. Dorta, P. Egli, F. Zürchner, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857. [2p] C. Hahn, A. Vitagliano, F. Giordano, R. Taube, Organometallics 1998, 17, 2060.
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9. For a recent review see: T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675. [2a] D. R. Coulson (Du Pont), US 3.758.586, 1973; Chem. Abstr. 1973, 79, 125808g. [2b] D. R. Coulson, Tetrahedron Lett. 1971, 429. [2c] L. S. Hegedus, Angew. Chem. 1988, 100, 1147; Angew. Chem. Int. Ed. Engl 1988, 27, 1113. [2d] A. L. Casalnuovo, J. L. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738. [2e] D. Steinborn, B. Thies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333. [2f] M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108. [2g] D. Selent, D. Scharfenberg-Pfeiffer, G. Reck, R. Taube, J. Organomet. Chem. 1991, 415, 417. [2h] M. R. Gagné, C. L. Stern, T. J. Marks, J. Am Chem. Soc 1992, 114, 275. [2i] J.-J. Brunet, D. Neibecker, K. Philippot, Tetrahedron Lett. 1993, 34, 3877. [2j] R. C. Larock, T. R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584. [2k] Y. Li, T. J. Marks, J. Am. Chem. Soc 1996, 118, 707. [2l] Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295. [2m] Y. W. Li, T J. Marks, Organometallics 1996, 15, 10212. [2n] C. Hahn, J. Sieler, R. Taube, Chem. Ber. 1997, 130, 939. [2o] R. Dorta, P. Egli, F. Zürchner, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857. [2p] C. Hahn, A. Vitagliano, F. Giordano, R. Taube, Organometallics 1998, 17, 2060.
10. For a recent review see: T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675. [2a] D. R. Coulson (Du Pont), US 3.758.586, 1973; Chem. Abstr. 1973, 79, 125808g. [2b] D. R. Coulson, Tetrahedron Lett. 1971, 429. [2c] L. S. Hegedus, Angew. Chem. 1988, 100, 1147; Angew. Chem. Int. Ed. Engl 1988, 27, 1113. [2d] A. L. Casalnuovo, J. L. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738. [2e] D. Steinborn, B. Thies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333. [2f] M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108. [2g] D. Selent, D. Scharfenberg-Pfeiffer, G. Reck, R. Taube, J. Organomet. Chem. 1991, 415, 417. [2h] M. R. Gagné, C. L. Stern, T. J. Marks, J. Am Chem. Soc 1992, 114, 275. [2i] J.-J. Brunet, D. Neibecker, K. Philippot, Tetrahedron Lett. 1993, 34, 3877. [2j] R. C. Larock, T. R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584. [2k] Y. Li, T. J. Marks, J. Am. Chem. Soc 1996, 118, 707. [2l] Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295. [2m] Y. W. Li, T J. Marks, Organometallics 1996, 15, 10212. [2n] C. Hahn, J. Sieler, R. Taube, Chem. Ber. 1997, 130, 939. [2o] R. Dorta, P. Egli, F. Zürchner, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857. [2p] C. Hahn, A. Vitagliano, F. Giordano, R. Taube, Organometallics 1998, 17, 2060.
11. For a recent review see: T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675. [2a] D. R. Coulson (Du Pont), US 3.758.586, 1973; Chem. Abstr. 1973, 79, 125808g. [2b] D. R. Coulson, Tetrahedron Lett. 1971, 429. [2c] L. S. Hegedus, Angew. Chem. 1988, 100, 1147; Angew. Chem. Int. Ed. Engl 1988, 27, 1113. [2d] A. L. Casalnuovo, J. L. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738. [2e] D. Steinborn, B. Thies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333. [2f] M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108. [2g] D. Selent, D. Scharfenberg-Pfeiffer, G. Reck, R. Taube, J. Organomet. Chem. 1991, 415, 417. [2h] M. R. Gagné, C. L. Stern, T. J. Marks, J. Am Chem. Soc 1992, 114, 275. [2i] J.-J. Brunet, D. Neibecker, K. Philippot, Tetrahedron Lett. 1993, 34, 3877. [2j] R. C. Larock, T. R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584. [2k] Y. Li, T. J. Marks, J. Am. Chem. Soc 1996, 118, 707. [2l] Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295. [2m] Y. W. Li, T J. Marks, Organometallics 1996, 15, 10212. [2n] C. Hahn, J. Sieler, R. Taube, Chem. Ber. 1997, 130, 939. [2o] R. Dorta, P. Egli, F. Zürchner, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857. [2p] C. Hahn, A. Vitagliano, F. Giordano, R. Taube, Organometallics 1998, 17, 2060.
12. For a recent review see: T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675. [2a] D. R. Coulson (Du Pont), US 3.758.586, 1973; Chem. Abstr. 1973, 79, 125808g. [2b] D. R. Coulson, Tetrahedron Lett. 1971, 429. [2c] L. S. Hegedus, Angew. Chem. 1988, 100, 1147; Angew. Chem. Int. Ed. Engl 1988, 27, 1113. [2d] A. L. Casalnuovo, J. L. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738. [2e] D. Steinborn, B. Thies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333. [2f] M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108. [2g] D. Selent, D. Scharfenberg-Pfeiffer, G. Reck, R. Taube, J. Organomet. Chem. 1991, 415, 417. [2h] M. R. Gagné, C. L. Stern, T. J. Marks, J. Am Chem. Soc 1992, 114, 275. [2i] J.-J. Brunet, D. Neibecker, K. Philippot, Tetrahedron Lett. 1993, 34, 3877. [2j] R. C. Larock, T. R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584. [2k] Y. Li, T. J. Marks, J. Am. Chem. Soc 1996, 118, 707. [2l] Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295. [2m] Y. W. Li, T J. Marks, Organometallics 1996, 15, 10212. [2n] C. Hahn, J. Sieler, R. Taube, Chem. Ber. 1997, 130, 939. [2o] R. Dorta, P. Egli, F. Zürchner, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857. [2p] C. Hahn, A. Vitagliano, F. Giordano, R. Taube, Organometallics 1998, 17, 2060.
13. For a recent review see: T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675. [2a] D. R. Coulson (Du Pont), US 3.758.586, 1973; Chem. Abstr. 1973, 79, 125808g. [2b] D. R. Coulson, Tetrahedron Lett. 1971, 429. [2c] L. S. Hegedus, Angew. Chem. 1988, 100, 1147; Angew. Chem. Int. Ed. Engl 1988, 27, 1113. [2d] A. L. Casalnuovo, J. L. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738. [2e] D. Steinborn, B. Thies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333. [2f] M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108. [2g] D. Selent, D. Scharfenberg-Pfeiffer, G. Reck, R. Taube, J. Organomet. Chem. 1991, 415, 417. [2h] M. R. Gagné, C. L. Stern, T. J. Marks, J. Am Chem. Soc 1992, 114, 275. [2i] J.-J. Brunet, D. Neibecker, K. Philippot, Tetrahedron Lett. 1993, 34, 3877. [2j] R. C. Larock, T. R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584. [2k] Y. Li, T. J. Marks, J. Am. Chem. Soc 1996, 118, 707. [2l] Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295. [2m] Y. W. Li, T J. Marks, Organometallics 1996, 15, 10212. [2n] C. Hahn, J. Sieler, R. Taube, Chem. Ber. 1997, 130, 939. [2o] R. Dorta, P. Egli, F. Zürchner, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857. [2p] C. Hahn, A. Vitagliano, F. Giordano, R. Taube, Organometallics 1998, 17, 2060.
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15. For a recent review see: T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675. [2a] D. R. Coulson (Du Pont), US 3.758.586, 1973; Chem. Abstr. 1973, 79, 125808g. [2b] D. R. Coulson, Tetrahedron Lett. 1971, 429. [2c] L. S. Hegedus, Angew. Chem. 1988, 100, 1147; Angew. Chem. Int. Ed. Engl 1988, 27, 1113. [2d] A. L. Casalnuovo, J. L. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738. [2e] D. Steinborn, B. Thies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333. [2f] M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108. [2g] D. Selent, D. Scharfenberg-Pfeiffer, G. Reck, R. Taube, J. Organomet. Chem. 1991, 415, 417. [2h] M. R. Gagné, C. L. Stern, T. J. Marks, J. Am Chem. Soc 1992, 114, 275. [2i] J.-J. Brunet, D. Neibecker, K. Philippot, Tetrahedron Lett. 1993, 34, 3877. [2j] R. C. Larock, T. R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584. [2k] Y. Li, T. J. Marks, J. Am. Chem. Soc 1996, 118, 707. [2l] Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295. [2m] Y. W. Li, T J. Marks, Organometallics 1996, 15, 10212. [2n] C. Hahn, J. Sieler, R. Taube, Chem. Ber. 1997, 130, 939. [2o] R. Dorta, P. Egli, F. Zürchner, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857. [2p] C. Hahn, A. Vitagliano, F. Giordano, R. Taube, Organometallics 1998, 17, 2060.
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