Nickel-catalyzed allylic substitution of simple alkenes

Chemistry - An Asian Journal

Volumn 6, Issue 7, 2011, Pages 1860-1875

  Matsubara, Ryosuke ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

alkenes; allylic substitution; homogeneous catalysis; nickel; reaction mechanisms

Indexed keywords

ALLYLIC SUBSTITUTION; CATALYTIC PROCESS; HIGH SELECTIVITY; HOMOGENEOUS CATALYSIS; REACTION MECHANISM; STRUCTURAL MOTIFS; TRIFLATES;

CATALYSIS; NICKEL; PHOSPHORUS COMPOUNDS; REACTION KINETICS; SUBSTITUTION REACTIONS;

OLEFINS;

ALKENE; ALLYL COMPOUND; NICKEL; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY;

ALKENES; ALLYL COMPOUNDS; CATALYSIS; NICKEL; SILANES;

EID: 79959970462     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000875     Document Type: Article

References (95)

1. Alpha Olefins Applications Handbook (Eds.:, G.R. Lappin, J.D. Sauer,), Marcel Dekker, New York, 1989.
2. Special Issue Frontiers in Metal-Catalyzed Polymerization (Guest Ed.: J.A. Gladysz), Chem. Rev. 2000, 100, 1167-1682
3. Organometallic Catalysts and Olefin Polymerization (Ed.:, R. Blom,), Springer, New York, 2001.
4. C. Claver, P. W. N. M. van Leeuwen, Rhodium Catalyzed Hydroformylation, Kluwer Academic Publishers, Dordrecht, The Netherlands, 2000.
5. Handbook of Metathesis (Ed.:, R.H. Grubbs,), Wiley, New York, 2003
6. R. H. Grubbs, Tetrahedron 2004, 60, 7117
7. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564
8. Angew. Chem. Int. Ed. 2005, 44, 4490.
9. For reviews, see:, I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
10. B. Snider, in Comprehensive Organic Synthesis, Vol.2 (Eds.:, B.M. Trost, I. Fleming,), Pergamon Press, Oxford, 1991, pp. 527-561.
11. S. Ogoshi, M.-a. Oka, H. Kurosawa, J. Am. Chem. Soc. 2004, 126, 11802
12. S. Ogoshi, M. Ueta, T. Arai, H. Kurosawa, J. Am. Chem. Soc. 2005, 127, 12810
13. S. Ogoshi, T. Haba, M. Ohashi, J. Am. Chem. Soc. 2009, 131, 10350
14. S. Ogoshi, A. Nishimura, T. Haba, M. Ohashi, Chem. Lett. 2009, 38, 1166.
15. S.-S. Ng, T. F. Jamison, J. Am. Chem. Soc. 2005, 127, 14194
16. C.-Y. Ho, S.-S. Ng, T. F. Jamison, J. Am. Chem. Soc. 2006, 128, 5362
17. C.-Y. Ho, T. F. Jamison, Angew. Chem. 2007, 119, 796
18. Angew. Chem. Int. Ed. 2007, 46, 782
19. C.-Y. Ho, H. Ohmiya, T. F. Jamison, Angew. Chem. 2008, 120, 1919
20. Angew. Chem. Int. Ed. 2008, 47, 1893.
21. S.-S. Ng, C.-Y. Ho, K. D. Schleicher, T. F. Jamison, Pure Appl. Chem. 2008, 80, 929
22. C.-Y. Ho, K. D. Schleicher, C.-W. Chan, T. F. Jamison, Synlett 2009, 2565.
23. B. M. Trost, C. B. Lee, in Catalytic Asymmetric Synthesis II (Ed.:, I. Ojima,), Wiley-VCH, New York, 2000, pp. 593-650
24. J. Tsuji, Acc. Chem. Res. 1969, 2, 144
25. B. M. Trost, D. L. VanVranken, Chem. Rev. 1996, 96, 395
26. Z. Lu, S. Ma, Angew. Chem. 2008, 120, 264
27. Angew. Chem. Int. Ed. 2008, 47, 258.
28. B. M. Trost, Tetrahedron 1977, 33, 2615.
29. For example, see:, M. Braun, T. Meier, F. Laicher, P. Meletis, M. Fiden, Adv. Synth. Catal. 2008, 350, 303.
30. For example, see:, X. Zhao, D. Liu, W. Zhang, Tetrahedron 2009, 65, 512.
31. C. Chuit, H. Felkin, C. Frajerman, G. Roussi, G. Swierczewski, J. Organomet. Chem. 1977, 127, 371
32. G. Consiglio, F. Morandini, O. Piccolo, J. Chem. Soc. Chem. Commun. 1983, 112
33. G. Consiglio, A. Indolese, Organometallics 1991, 10, 3425
34. N. Nomura, T. V. RajanBabu, Tetrahedron Lett. 1997, 38, 1713
35. E. Gomez-Bengoa, N. M. Heron, M. T. Didiuk, C. A. Luchaco, A. H. Hoveyda, J. Am. Chem. Soc. 1998, 120, 7649.
36. H. Yasui, K. Mizutani, H. Yorimitsu, K. Oshima, Tetrahedron 2006, 62, 1410.
37. B. M. Trost, M. D. Spagnol, J. Chem. Soc. Perkin Trans. 1 1995, 2083 and references therein.
38. M. Moreno-Manas, F. Pajuelo, R. Pleixats, J. Org. Chem. 1995, 60, 2396
39. H. Ohmiya, Y. Makida, T. Tanaka, M. Sawamura, J. Am. Chem. Soc. 2008, 130, 17276
40. T. Mino, K. Kajiwara, Y. Shirae, M. Sakamoto, T. Fujita, Synlett 2008, 2711
41. T. Nishikata, B. H. Lipshutz, J. Am. Chem. Soc. 2009, 131, 12103.
42. S. R. Wilson, P. A. Zucker, J. Org. Chem. 1988, 53, 4682
43. B. M. Trost, G. D. Probst, A. Schoop, J. Am. Chem. Soc. 1998, 120, 9228
44. G. Hilt, F.-X. du Mesnil, S. Lüers, Angew. Chem. 2001, 113, 408
45. Angew. Chem. Int. Ed. 2001, 40, 387
46. C. J. Morten, T. F. Jamison, Tetrahedron 2009, 65, 6648
47. B. Moreau, J. Y. Wu, T. Ritter, Org. Lett. 2009, 11, 337.
48. N. Tsukada, T. Sato, Y. Inoue, Chem. Commun. 2001, 237
49. N. Tsukada, T. Sato, Y. Inoue, Chem. Commun. 2003, 2404.
50. W. Oppolzer, M. Bedoya-Zurita, C. Y. Switzer, Tetrahedron Lett. 1988, 29, 6433
51. W. Oppolzer, Angew. Chem. 1989, 101, 39
52. Angew. Chem. Int. Ed. Engl. 1989, 28, 38.
53. R. Matsubara, T. F. Jamison, J. Am. Chem. Soc. 2010, 132, 6880.
54. C. A. Tolman, Chem. Rev. 1977, 77, 313
55. M. M. Rahman, H.-Y. Liu, K. Eriks, A. Prock, W. P. Giering, Organometallics 1989, 8, 1.
56. It is known that a cationic Ni-H complex catalyzes olefin isomerization. For example, see:, A. R. O'Connor, S. A. Urbin, R. A. Moorhouse, P. S. White, M. Brookhart, Organometallics 2009, 28, 2372.
57. For examples of nickel-catalyzed coupling reactions using allylic ethers, see:, N. Nomura, T. V. RajanBabu, Tetrahedron Lett. 1997, 38, 1713. Also see Ref.[14c].
58. J. Drexler, R. Lindermayer, M. A. Hassan, J. Sauer, Tetrahedron Lett. 1985, 26, 2555.
59. 0 precursor for many nickel complexes., V. W. Dreissig, H. Dietrich, Acta Crystallogr. Sect. B 1968, 24, 108.
60. T. Yamamoto, J. Ishizu, A. Yamamoto, J. Am. Chem. Soc. 1981, 103, 6863.
61. 31PNMR spectrum. We cannot rule out the possibility that carbonate is a counter anion instead of methoxide., F. Ozawa, T. Son, S. Ebina, K. Osakada, A. Yamamoto, Organometallics 1992, 11, 171.
62. G. M. DiRenzo, P. S. White, M. Brookhart, J. Am. Chem. Soc. 1996, 118, 6225
63. S. Mecking, W. Keim, Organometallics 1996, 15, 2650
64. K. L. Bray, J. P. H. Charmant, I. J. S. Fairlamb, G. C. Lloyd-Jones, Chem. Eur. J. 2001, 7, 4205
65. D. J. Cárdenas, M. Alcamí, F. Cossío, M. Méndez, A. M. Echavarren, Chem. Eur. J. 2003, 9, 96
66. J. Joseph, T. V. RajanBabu, E. D. Jemmis, Organometallics 2009, 28, 3552.
67. S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763
68. J. W. J. Kennedy, D. G. Hall, Angew. Chem. 2003, 115, 4880
69. Angew. Chem. Int. Ed. 2003, 42, 4732.
70. J. Godschalx, J. K. Stille, Tetrahedron Lett. 1980, 21, 2599
71. B. M. Trost, E. Keinan, Tetrahedron Lett. 1980, 21, 2595
72. A. Goliaszewski, J. Schwartz, J. Am. Chem. Soc. 1984, 106, 5028
73. A. Goliaszewski, J. Schwartz, Tetrahedron 1985, 41, 5779
74. A. Goliaszewski, J. Schwartz, Organometallics 1985, 4, 417
75. M. Murakami, T. Kato, T. Mukaiyama, Chem. Lett. 1987, 1167
76. H. Nakamura, M. Bao, Y. Yamamoto, Angew. Chem. 2001, 113, 3308
77. Angew. Chem. Int. Ed. 2001, 40, 3208
78. P. H. Lee, S.-y. Sung, K. Lee, S. Chang, Synlett 2002, 0146
79. P. H. Lee, E. Shim, K. Lee, D. Seomoon, S. Kim, Bull. Korean Chem. Soc. 2005, 26, 157
80. E. F. Flegeau, U. Schneider, S. Kobayashi, Chem. Eur. J. 2009, 15, 12247.
81. B. M. Trost, D. B. Horne, M. J. Woltering, Chem. Eur. J. 2006, 12, 6607
82. M. Pineschi, F. Bertolini, V. D. Bussolo, P. Crotti, Curr. Org. Synth. 2009, 6, 290.
83. S. Crotti, F. Bertolini, F. Macchia, M. Pineschi, Org. Lett. 2009, 11, 3762. For nickel-catalyzed borylative ring opening of vinylcyclopropanes, see
84. Y. Sumida, H. Yorimitsu, K. Oshima, Org. Lett. 2008, 10, 4677.
85. B. M. Trost, G. A. Molander, J. Am. Chem. Soc. 1981, 103, 5969.
86. E. Carmona, J. M. Marín, M. Paneque, M. L. Poveda, Organometallics 1987, 6, 1757
87. E. Carmona, J. M. Marín, P. Palma, M. Paneque, M. L. Poveda, Inorg. Chem. 1989, 28, 1895
88. E. Carmona, M. Paneque, M. L. Poveda, Polyhedron 1989, 8, 285
89. T. J. Anderson, D. A. Vicic, Organometallics 2004, 23, 623
90. Y. Chen, G. Wu, G. C. Bazan, Angew. Chem. 2005, 117, 1132
91. Angew. Chem. Int. Ed. 2005, 44, 1108.
92. D. A. Mundal, K. E. Lutz, R. J. Thomson, Org. Lett. 2009, 11, 465.
93. T. Velasco-Torrijos, P. V. Murphy, Org. Lett. 2004, 6, 3961.
94. L. Ferrié, S. Reymond, P. Capdevielle, J. Cossy, Org. Lett. 2007, 9, 2461.
95. H. Matsuhashi, S. Asai, K. Hirabayashi, Y. Hatanaka, A. Mori, T. Hiyama, Bull. Chem. Soc. Jpn. 1997, 70, 1943.