Ni(II) salts and 2-propanol effect catalytic reductive coupling of epoxides and alkynes

Organic Letters

Volumn 13, Issue 15, 2011, Pages 4140-4143

  Beaver, Matthew G ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; ALKYNE; BROMIDE; EPOXIDE; NICKEL;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

2-PROPANOL; ALKYNES; BROMIDES; CATALYSIS; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; NICKEL; OXIDATION-REDUCTION;

EID: 79961039089     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201702a     Document Type: Article

References (64)

1. For reviews, see: Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890-3908
2. Montgomery, J.; Sormunen, G. J. Top. Curr. Chem. 2007, 279, 1-23
3. Moslin, R. M.; Miller-Moslin, K.; Jamison, T. F. Chem. Commun. 2007, 4441-4449
4. Kimura, M.; Tamaru, Y. Top. Curr. Chem. 2007, 279, 173-207
5. Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346-1416
6. For selected examples of recent advances in Ni-catalyzed C-C bond forming reactions, see: Malik, H. A.; Sormunen, G. J.; Montgomery, J. J. Am. Chem. Soc. 2010, 132, 6304-6305
7. Matsubara, R.; Jamison, T. F. J. Am. Chem. Soc. 2010, 132, 6880-6881
8. Cho, H. Y.; Morken, J. P. J. Am. Chem. Soc. 2010, 132, 7576-7577
9. Zhou, C.-Y.; Zhu, S.-F.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc. 2010, 132, 10955-10957
10. Li, W.; Chen, N.; Montgomery, J. Angew. Chem., Int. Ed. 2010, 49, 8712-8716
11. Ho, C.-Y.; He, L. Angew. Chem., Int. Ed. 2010, 49, 9182-9186
12. Taylor, B. L. H.; Swift, E. C.; Waetzig, J. D.; Jarvo, E. R. J. Am. Chem. Soc. 2011, 133, 389-391
13. Hoshimoto, Y.; Ohashi, M.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 4668-4671
14. For selected examples of C-C bond forming methods employing Ni(II) precatalysts, see: Watson, M. P.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 12594-12595
15. Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc. 2008, 130, 14422-14423
16. Williams, C. M.; Johnson, J. B.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14936-14937
17. Everson, D. A.; Shrestha, R.; Weix, D. J. J. Am. Chem. Soc. 2010, 132, 920-921
18. Lundin, P. M.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 11027-11029
19. Owston, N. A.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 11908-11909
20. Alcohols bearing β-hydrogen atoms have proven to be competent reducing agents in Ni-catalyzed reductive coupling reactions: Herath, A.; Li, W.; Montgomery, J. J. Am. Chem. Soc. 2008, 130, 469-471
21. Li, W.; Herath, A.; Montgomery, J. J. Am. Chem. Soc. 2009, 131, 17024-17029
22. Phillips, J. H.; Montgomery, J. Org. Lett. 2010, 12, 4556-4559
23. For additional examples of i -PrOH-mediated reductive C-C bond-forming reactions, see: Bower, J. F.; Skucas, E.; Patman, R. L.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 15134-15135
24. Bower, J. F.; Patman, R. L.; Krische, M. J. Org. Lett. 2008, 10, 1033-1035
25. Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6338-6339
26. Patman, R. L.; Chaulagain, M. R.; Williams, V. M.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2066-2067
27. Molinaro, C.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 8076-8077
28. For examples of the utility of Ni-catalyzed alkyne-epoxide reductive coupling in the context of natural product synthesis, see: O'Brien, K. C.; Colby, E. A.; Jamison, T. F. Tetrahedron 2005, 61, 6243-6248
29. Woodin, K. S.; Jamison, T. F. J. Org. Chem. 2007, 72, 7451-7454
30. Sparling, B. A.; Simpson, G. L.; Jamison, T. F. Tetrahedron 2009, 65, 3270-3280
31. Trenkle, J. D.; Jamison, T. F. Angew. Chem., Int. Ed. 2009, 48, 5366-5368
32. Reductive opening of epoxides has also been observed under titanocene catalysis: Gansäuer, A.; Pierobon, M.; Bluhm, H. Angew. Chem., Int. Ed. 1998, 37, 101-103
33. Gansäuer, A.; Bluhm, H.; Pierobon, M. J. Am. Chem. Soc. 1998, 120, 12849-12859
34. For example, see: Vilotijevic, I.; Jamison, T. F. Science 2007, 317, 1189-1192
35. Byers, J. A.; Jamison, T. F. J. Am. Chem. Soc. 2009, 131, 6383-6385
36. Morten, C. J.; Byers, J. A.; Van Dyke, A. R.; Vilotijevic, I.; Jamison, T. F. Chem. Soc. Rev. 2009, 38, 3175-3192
37. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Am. Chem. Soc. 1985, 107, 1082-1083
38. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Org. Chem. 1985, 50, 5096-5099
39. Yamada, T.; Morisseau, C.; Maxwell, J. E.; Argiriadi, M. A.; Christianson, D. W.; Hammock, B. D. J. Biol. Chem. 2000, 275, 23082-23088
40. Omoto, K.; Fujimoto, H. J. Org. Chem. 2000, 65, 2464-2471
41. Fleming, E. M.; Quigley, C.; Rozas, I.; Connon, S. J. J. Org. Chem. 2008, 73, 948-956
42. Wurst, J. M.; Liu, G.; Tan, D. S. J. Am. Chem. Soc. 2011, 133, 7916-7925
43. For selected reviews describing transition-metal-catalyzed transfer hydrogenation, see: Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051-1069
44. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102
45. Bower, J. F.; Kim, I. S.; Patman, R. L.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 34-46
46. Ananikov, V. P.; Gayduk, K. A.; Starikova, Z. A.; Beletskaya, I. P. Organometallics 2010, 29, 5098-5102
47. Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009-3013
48. Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177-2180
49. Fors, B. P.; Krattiger, P.; Strieter, E.; Buchwald, S. L. Org. Lett. 2008, 10, 3505-3508
50. Sacco, A.; Mastrorilli, P. J. Chem. Soc., Dalton Trans. 1994, 2761-2764
51. Hubert-Pfalzgraf, L. G.; Kessler, V. G.; Vaissermann, J. Polyhedron 1997, 16, 4197-4203
52. Phosphine-catalyzed conjugate addition of i -PrOH to the alkynoate was observed, which has been reported previously: Inanaga, J.; Baba, Y.; Hanamoto, T. Chem. Lett. 1993, 241-244
53. Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035-1050
54. Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2916
55. Aye, K.-T.; Gelmini, L.; Payne, N. C.; Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1990, 112, 2464-2465
56. Bäckvall, J.-E.; Bökman, F.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 534-538
57. Kulasegaram, S.; Kulawiec, R. J. Tetrahedron 1998, 54, 1361-1374
58. 4)] complexes has also been observed to occur with inversion of configuration: Church, T. L.; Getzler, Y. D. Y. L.; Coates, G. W. J. Am. Chem. Soc. 2006, 128, 10125-10133
59. Bäckvall, J.-E.; Karlsson, O.; Ljunggren, S. O. Tetrahedron Lett. 1980, 21, 4985-4988
60. Oxidative addition of tosyl-aziridines with Ni(0) has been observed to occur with inversion of configuration: Lin, B. L.; Clough, C. R.; Hillhouse, G. L. J. Am. Chem. Soc. 2002, 124, 2890-2891
61. The mechanism of migratory insertion is generally accepted to occur with retention of configuration at the metal-bonded carbon. For the seminal study, see: Bock, P. L.; Boschetto, D. J.; Rasmussen, J. R.; Demers, J. P.; Whitesides, G. M. J. Am. Chem. Soc. 1974, 96, 2814-2825 For further discussion of migratory insertion as it pertains to the stereochemical outcome of transition-metal- mediated processes, see: Lau, K. S. Y.; Wong, P. K.; Stille, J. K. J. Am. Chem. Soc. 1976, 98, 5832-5840
62. Spencer, J.; Pfeffer, M. Tetrahedron: Asymmetry 1995, 6, 419-426
63. Malinakova, H. C. Chem.-Eur. J. 2004, 10, 2636-2646
64. Lu, G.; Malinakova, H. C. J. Org. Chem. 2004, 69, 4701-4715