Direct vinylation of alcohols or aldehydes employing alkynes as vinyl donors: A ruthenium catalyzed C-C bond-forming transfer hydrogenation

Journal of the American Chemical Society

Volumn 131, Issue 6, 2009, Pages 2066-2067

  Patman, Ryan L ^a   Chaulagain, Mani Raj ^a   Williams, Vanessa M ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CARBONYLATION; HYDROGENATION; ORGANIC ACIDS; RUTHENIUM;

2-BUTYNE; ALIPHATIC ALCOHOL; ALLYLIC ALCOHOL; BENZYLIC; C-C BONDS; INTRAMOLECULAR COUPLING; NONSYMMETRIC; OXIDATION LEVEL; REDUCTANT; REGIOISOMERS; TRANSFER HYDROGENATIONS; VINYLATION; [CARBONYL;

ALDEHYDES;

2 BUTANOL; 2 PROPANOL; 4 NITROBENZOIC ACID; ACETYLENE DERIVATIVE; ACETYLENIC ALDEHYDE; ALCOHOL DERIVATIVE; ALDEHYDE; ALIPHATIC CARBOXYLIC ACID; ALKENE; BENZILIC ACID; CARBON; CARBONYL DERIVATIVE; ELECTROPHILE; FORMIC ACID; HYDROGEN; IRIDIUM; NICKEL; RHODIUM; RUTHENIUM COMPLEX; SODIUM IODIDE; TITANIUM; UNCLASSIFIED DRUG; VINYL DERIVATIVE; ALKYNE; RUTHENIUM;

ALLYLATION; ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; CHEMICAL BOND; COMPLEX FORMATION; CROSS COUPLING REACTION; CYCLIZATION; ELECTRON TRANSPORT; ENERGY YIELD; HEATING; HYDROGENATION; MOLECULAR INTERACTION; OXIDATION; STEREOCHEMISTRY; STOICHIOMETRY; CHEMISTRY; SYNTHESIS;

ALCOHOLS; ALDEHYDES; ALKYNES; CATALYSIS; HYDROGENATION; RUTHENIUM; VINYL COMPOUNDS;

EID: 67749135569     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja809456u     Document Type: Article

References (57)

1. (a) Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823.
2. (b) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
3. For enantioselective catalytic addition of vinylzinc reagents to aldehydes, see: (a) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170.
4. (b) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593.
5. (c) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257.
6. (d) Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197.
7. (e) Oppolzer, W.; Radinov, R. N.; De Brabander, J. Tetrahedron Lett. 1995, 36, 2607.
8. (f) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454.
9. (g) Oppolzer, W.; Radinov, R. N.; El-Sayed, E J. Org. Chem. 2001, 66, 4766.
10. (h) Dahmen, S.; Brase, S. Org. Lett. 2001, 3, 4119.
11. Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225.
12. (j) Ji, J.-X.; Qiu, L.-Q.; Yip, C. W.; Chan, A. S. C. J. Org. Chem. 2003, 68, 1589.
13. (k) Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2003,125, 10677.
14. (l) Jeon, S.-J.; Chen, Y. K.; Walsh, P. J. Org. Lett. 2005, 7, 1729.
15. (m) Lauterwasser, F.; Gall, J.; Hoefener, S.; Bräse, S. Adv. Synth. Catal. 2006, 348, 2068.
16. (n) Jeon, S.-J.; Fisher, E. L.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2006, 128, 9618.
17. (o) Salvi, L.; Jeon, S.-J.; Fisher, E. L.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2007, 129, 16119.
18. For reviews on catalytic enantioselective aldehyde vinylation using organozinc reagents, see: (a) Wipf, P.; Kendall, C. Chem. - Eur. J. 2002, 8, 1778.
19. (b) Wipf, P.; Nunes, R. L. Tetrahedron 2004, 60, 1269.
20. For catalytic enantioselective ketone vinylation using organozinc reagents, see: (a) Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 6538.
21. (b) Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 8355.
22. Jeon, S.-J.; Li, H.; Garcia, C.; La Rochelle, L. K.; Walsh, P. J. J. Org. Chem. 2005, 70, 448.
23. Ojima, I.; Tzamarioudaki, M.; Tsai, C.-Y. J. Am. Chem. Soc. 1994,116, 3643.
24. (a) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787 For an aligned study, see:
25. (b) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785.
26. For intramolecular nickel catalyzed alkyne-carbonyl reductive coupling, see: (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065.
27. (b) Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 6098.
28. (c) Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6950.
29. Knapp-Reed, B.; Mahandru, G. M.; Montgomery, J. J. Am. Chem. Soc. 2005,127, 13156.
30. For intermolecular Ni-catalyzed alkyne-carbonyl reductive coupling, see: (a) Huang, W.-S.; Chan, J.; Jamison, T. F. Org. Lett. 2000, 2, 4221.
31. (b) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442.
32. Takai, K.; Sakamoto, S.; Isshiki, T. Org. Lett. 2003, 5, 653.
33. Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698.
34. A review of Ni-catalyzed alkyne-carbonyl reductive coupling: Montgomery, J.; Sormunen, G. J. Top. Curr. Chem. 2007, 279, 1.
35. For reviews of hydrogen-mediated C-C coupling, see: (a) Ngai, M.-Y.; Kong, J.-R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
36. (b) Skucas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394.
37. Shibahara, F.; Krische, M. J. Chem. Lett. 2008, 37, 1102.
38. For hydrogenative coupling of nonconjugated alkynes to carbonyl compounds and imines, see: (a) Rhee, J.-U.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 10674.
39. (b) Skucas, E.; Kong, J. R.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 7242.
40. Barchuk, A.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 8432.
41. Ngai, M.-Y.; Barchuk, A.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12644.
42. (e) Han, S. B.; Kong, J.-R.; Krische, M. J. Org. Lett. 2008, 10, 4133.
43. For hydrogenative coupling of 1,3-enynes to carbonyl compounds and imines, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4664.
44. (b) Kong, J.-R.; Cho, C.-W.; Krische, M. J. J. Am. Chem. Soc. 2005, 127, 11269.
45. Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.
46. Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16448.
47. (e) Hong, Y.-T.; Cho, C.-W.; Skucas, E.; Krische, M. J. Org. Lett. 2007, 9, 3745.
48. For Ir-catalyzed transfer hydrogenative C-C coupling, see: (a) Bower, J. F.; Skucas, E.; Patman, R. L.; Krische, M. J. J. Am. Chem. Soc. 2007,129, 15134.
49. (b) Bower, J. F.; Patman, R. L.; Krische, M. J. Org. Lett. 2008, 10, 1033.
50. For Ru-catalyzed transfer hydrogenative C-C coupling, see: (a) Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6338.
51. (b) Ngai, M.-Y.; Skucas, E.; Krische, M. J. Org. Lett. 2008, 10, 2705.
52. Patman, R. L.; Williams, V. M.; Bower, J. F.; Krische, M. J. Angew. Chem.,Int. Ed. 2008, 47, 5220.
53. Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14120.
54. 3 and trends in substrate scope suggest these processes involve alcohol dehydrogenation-reductive Prins addition: Shi, L.; Tu, Y.- Q.; Wang, M.; Zhang, F.-M.; Fan, C.-A.; Zhao, Y.-M.; Xia, W. J. J. Am. Chem. Soc. 2005, 127, 10836.
55. Ni-catalyzed reductive coupling of 1,3-enynes to carbonyl compounds: (a) Miller, K. M.; Luanphaisarnnont, T.; Molinaro, C.; Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 4130.
56. (b) Miller, K. M.; Jamison, T. F. Org. Lett. 2005, 7, 3077.
57. Miller, K. M.; Colby, E. A.; Woodin, K. S.; Jamison, T. F. Adv. Synth. Catal. 2005, 347, 1533 (also see ref 8d).