Branch-selective reductive coupling of 2-vinyl pyridines and imines via rhodium catalyzed C-C bond forming hydrogenation

Journal of the American Chemical Society

Volumn 130, Issue 38, 2008, Pages 12592-12593

  Komanduri, Venukrishnan ^a   Grant, Christopher D ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; IMINE; PYRIDINE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG; VINYL AZINE DERIVATIVE; VINYL DERIVATIVE; VINYLPYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CROSS COUPLING REACTION; DEUTERON NUCLEAR MAGNETIC RESONANCE; HYDROGENATION; ISOMERIZATION; NONHUMAN; OXIDATION REDUCTION REACTION; PRODUCT RECOVERY; STILLE REACTION; SUZUKI REACTION;

CATALYSIS; HYDROGENATION; IMINES; OXIDATION-REDUCTION; PHOSPHINES; PYRIDINES; RHODIUM;

EID: 52449127699     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805056g     Document Type: Article

References (42)

1. For an excellent review, see: (a) Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337.
2. Bonnet, V.; Mongin, F.; Trécourt, F.; Breton, G.; Marsais, F.; Knochel, P.; Quéguiner, G. Synlett 2002, 1008. As stated in ref 1 of the preceding article, "according to the MDL Drug Data Report, the most widespread heterocycles in pharmaceutically active compounds are pyridine (out of 15 000 structures), imidazole (out of 11 000), indole (out of 6700), and pyrimidine (out of 4500)."
3. Campeau, L.-C.; Fagnou, K. Chem. Soc. Rev. 2007, 36, 1058.
4. (a) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 5332.
5. (b) Nakao, Y.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2008, 130, 2448.
6. (a) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358.
7. (b) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123.
8. (c) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
9. (a) Selimov, F. A.; Ptashko, O. A.; Fatykhov, A. A.; Khalikova, N. R.; Dzhemilev, U. M. Russ. Chem. Bull. 1993, 42, 913.
10. (b) Lim, Y.-G.; Kang, J.-B.; Kim, Y.-H. Chem. Commun. 1996, 585.
11. (c) Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1998, 699.
12. (d) Lim, Y.-G.; Han, J.-S.; Kang, J.-B. Bull. Korean Chem. Soc. 1998, 19, 1143.
13. (e) Lim, Y.-G.; Kang, J.-B.; Koo, B. T. Tetrahedron Lett. 1999, 40, 7691.
14. (f) Lim, Y.-G.; Han; Jong-Soo; Koo, Bon Tak.; Kang, Jung-Bu. Bull. Korean Chem. Soc. 1999, 20, 1097.
15. (g) Lim, Y.-G.; Kang, J.-B.; Lee, K.; Kim, Y. H. Heteroatom Chem. 2002, 13, 346.
16. (h) Aïssa, C.; Fürstner, A. J. Am. Chem. Soc. 2007, 129, 14836.
17. Vinylpyridines engage in highly branch-selective hydroformylation: Settambolo, R.; Pucci, S.; Bertozzi, S.; Lazzaroni, R. J. Organomet. Chem. 1995, 489, C50.
18. (b) Botteghi, C.; Marchetti, M.; Paganelli, S.; Sechi, B. J. Mol. Catal. 1997, 118, 173.
19. For Heck reactions of 2-vinylpyridine, see: (a) Kasahara, A.; Izumi, T.; Takeda, T.; Imamura, H. Bull. Chem. Soc. Jpn. 1974, 47, 183.
20. (b) Berthiol, F.; Doucet, H.; Santelli, M. Synlett 2003, 841.
21. (c) Narahashi, H.; Yamamoto, A.; Shimizu, I. Chem. Lett. 2004, 33, 348.
22. For ruthenium catalyzed cross-metathesis reactions of vinylpyridine, see: (a) Chatterjee, A. K.; Toste, F. D.; Choi, T.-L.; Grubbs, R. H. Adv. Synth. Catal. 2002, 344, 634.
23. For selected reviews of hydrogenative C-C coupling, see: (a) Ngai, M.-Y.; Kong, J.-R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
24. (b) Iida, H.; Krische, M. J. Top. Curr. Chem. 2007, 279, 77.
25. (c) Skucas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394.
26. (a) Hong, Y.-T.; Barchuk, A.; Krische, M. J. Angew. Chem., Int. Ed 2006, 128, 6885.
27. (b) See also: Kokubo, K.; Miura, M.; Nomura, M. Organometallics 1995, 14, 4521.
28. For hydrogen-mediated reductive aldol addition, see: (a) Jang, H. Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
29. (b) Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5, 1143.
30. (c) Koech, P. K.; Krische, M. J. Org. Lett. 2004, 6, 691.
31. (d) Marriner, G. A.; Garner, S. A.; Jang, H. Y.; Krische, M. J. J. Org. Chem. 2004, 69, 1380.
32. (e) Jung, C. K.; Garner, S. A.; Krische, M. J. Org. Lett. 2006, 8, 519.
33. (f) Han, S. B.; Krische, M. J. Org. Lett. 2006, 8, 5657.
34. (g) Jung, C. K.; Krische, M, J. J. Am. Chem. Soc. 2006, 128, 17051.
35. (h) Bee, C.; Han, S. B.; Hassan, A.; Iida, H.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 2747.
36. For hydrogen-mediated reductive Mannich addition, see: (a) Garner, S. A.; Krische, M. J. J. Org. Chem. 2007, 72, 5843.
37. For tri-2-furylphosphine and triphenylarsine effects in metal catalyzed reactions, see: (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
38. (b) Farina, V. Pure Appl. Chem. 1996, 68, 73.
39. (c) Anderson, N. G.; Keay, B. A. Chem. Rev. 2001, 101, 997.
40. 3P enforces high levels of syndiastereoselectivity. Given the structural homology of vinyl ketones and 2-vinyl azines, it is not surprising that analogous ligand effects are observed.
41. Coupling of 2,3-diphenyl-5-vinylpyrazine to imine 2f under standard conditions provides the branched adduct in 35% yield and 5:1 dr.
42. The stoichiometric reaction of isolated rhodacyclopentadienes with elemental hydrogen delivers the product of hydrogenolysis: Müller, E.; Thomas, R.; Zountsas, G. Liebigs Ann. Chem. 1972, 758, 16.