Quick installation of a 1,4-difunctionality via regioselective nickel-catalyzed reductive coupling of ynoates and aldehydes

Journal of Organic Chemistry

Volumn 77, Issue 18, 2012, Pages 8303-8309

  Rodrigo, Sanjeewa K ^a   Guan, Hairong ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC AMOUNTS; CATALYTIC PROCESS; FIVE-MEMBERED RINGS; INTERMOLECULAR REDUCTIVE COUPLING; METALLACYCLES; MULTICOMPONENT COUPLING REACTIONS; N-HETEROCYCLIC CARBENE LIGANDS; REDUCTIVE COUPLINGS; REGIO-SELECTIVE;

ALDEHYDES; DEUTERIUM; LIGANDS; REGIOSELECTIVITY;

ORGANIC COMPOUNDS;

ALDEHYDE DERIVATIVE; CARBENE; DEUTERIUM; HETEROCYCLIC COMPOUND; LIGAND; NICKEL; OXYGEN; SILANE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COUPLING FACTOR; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 84868121437     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301790q     Document Type: Article

References (62)

1. Seebach, D. Angew. Chem., Int. Ed. 1979, 18, 239.
2. (a) Johnson, J. S. Angew. Chem., Int. Ed. 2004, 43, 1326.
3. (b) Vora, H. U.; Rovis, T. Aldrichim. Acta 2011, 44, 3.
4. (c) Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691.
5. (d) Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011, 40, 5336.
6. (e) Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511.
7. (a) Guan, H. Curr. Org. Chem. 2008, 12, 1406.
8. (b) Zhang, J.; Krause, J. A.; Huang, K.-W.; Guan, H. Organometallics 2009, 28, 2938.
9. Csákÿ, A. G.; Plumet, J. Chem. Soc. Rev. 2001, 30, 313.
10. (a) Baran, P. S.; DeMartino, M. P. Angew. Chem., Int. Ed. 2006, 45, 7083.
11. (b) DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 11546.
12. (a) Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14082.
13. (b) Yoo, E. J.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 17378.
14. (c) Hasegawa, N.; Charra, V.; Inoue, S.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 8070.
15. Ni-catalyzed reactions: (a) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
16. (b) Ikeda, S. Angew. Chem., Int. Ed. 2003, 42, 5120.
17. (c) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
18. (d) Montgomery, J.; Sormunen, G. J. Top. Curr. Chem. 2007, 279
19. (e) Moslin, R. M.; Miller-Moslin, K.; Jamison, T. F. Chem. Commun. 2007, 4441.
20. (f) Rhee, J. U.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 10674.
21. (g) Ngai, M.-Y.; Kong, J.-R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
22. (h) Skucas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394.
23. Ti-mediated stoichiometric reactions: (a) Reichard, H. A.; McLaughlin, M.; Chen, M. Z.; Micalizio, G. C. Eur. J. Org. Chem. 2010, 391.
24. Sm-mediated stoichiometric reactions: (b) Inanaga, J.; Katsuki, J.; Ujikawa, O.; Yamaguchi, M. Tetrahedron Lett. 1991, 32, 4921.
25. (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065.
26. (b) Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 6098.
27. (c) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698.
28. (d) Sa-ei, K.; Montgomery, J. Org. Lett. 2006, 8, 4441.
29. (e) Chaulagain, M. R.; Sormunen, G. J.; Montgomery, J. J. Am. Chem. Soc. 2007, 129, 9568.
30. (f) Baxter, R. D.; Montgomery, J. J. Am. Chem. Soc. 2008, 130, 9662.
31. (g) Malik, H. A.; Chaulagain, M. R.; Montgomery, J. Org. Lett. 2009, 11, 5734.
32. (h) Malik, H. A.; Sormunen, G. J.; Montgomery, J. J. Am. Chem. Soc. 2010, 132, 6304.
33. (a) Huang, W.-S.; Chan, J.; Jamison, T. F. Org. Lett. 2000, 2, 4221.
34. (b) Miller, K. M.; Molinaro, C.; Jamison, T. F. Tetrahedron: Asymmetry 2003, 14, 3619.
35. (c) Colby, E. A.; Jamison, T. F. J. Org. Chem. 2003, 68, 156.
36. (d) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442.
37. (e) Miller, K. M.; Luanphaisarnnont, T.; Molinaro, C.; Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 4130.
38. (f) Moslin, R. M.; Jamison, T. F. Org. Lett. 2006, 8, 455.
39. (a) Takai, K.; Sakamoto, S.; Isshiki, T. Org. Lett. 2003, 5, 653.
40. (b) Takai, K.; Sakamoto, S.; Isshiki, T.; Kokumai, T. Tetrahedron 2006, 62, 7534.
41. (c) Saito, N.; Katayama, T.; Sato, Y. Org. Lett. 2008, 10, 3829.
42. (d) Yang, Y.; Zhu, S.-F.; Zhou, C.-Y.; Zhou, Q.-L. J. Am. Chem. Soc. 2008, 130, 14052.
43. (e) Saito, N.; Sugimura, Y.; Sato, Y. Org. Lett. 2010, 12, 3494.
44. Carbon-carbon bond formation in the Ti-mediated coupling of ynoates and alkynes has been shown to occur at the β-carbon of ynoates; see: Hamada, T.; Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1999, 121, 7342.
45. (a) Nicolaou, K. C.; Pavia, M. R.; Seitz, S. P. J. Am. Chem. Soc. 1981, 103, 1224.
46. (b) Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem. 1995, 60, 5386.
47. (c) Naka, T.; Koide, K. Tetrahedron Lett. 2003, 44, 443.
48. (d) Meta, C. T.; Koide, K. Org. Lett. 2004, 6, 1785.
49. The strategy of adding a phosphine ligand to stabilize the active catalyst has been previously used; see: Sawaki, R.; Sato, Y.; Mori, M. Org. Lett. 2004, 6, 1131.
50. Hiyama Cross-Coupling Reaction. In Name Reactions for Homologations; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009; Part 1, p 33.
51. (a) McCarren, P. R.; Liu, P.; Cheong, P. H.-Y.; Jamison, T. F.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 6654.
52. (b) Liu, P.; McCarren, P.; Cheong, P. H.-Y.; Jamison, T. F.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 2050.
53. (c) Liu, P.; Montgomery, J.; Houk, K. N. J. Am. Chem. Soc. 2011, 133, 6956.
54. Baxter, R. D.; Montgomery, J. J. Am. Chem. Soc. 2011, 133, 5728.
55. Ogoshi, S.; Arai, T.; Ohashi, M.; Kurosawa, H. Chem. Commun. 2008, 1347.
56. Martinho Simões, J. A.; Beauchamp, J. L. Chem. Rev. 1990, 90, 629.
57. Rooke, D. A.; Ferreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 3225.
58. Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. 1985, 24, 94.
59. Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504.
60. Lavallo, V.; Canac, Y.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Science 2006, 312, 722.
61. Jurkauskas, V.; Sadighi, J. P.; Buchwald, S. L. Org. Lett. 2003, 5, 2417.
62. Kim, S.; Chung, K. N.; Yang, S. J. Org. Chem. 1987, 52, 3917.