Nickel-catalyzed Mizoroki-Heck- versus Michael-type addition of organoboronic acids to α,β-unsaturated alkenes through fine-tuning of ligands

Chemistry - An Asian Journal

Volumn 2, Issue 11, 2007, Pages 1409-1416

  Lin, Pao Shun ^a   Jeganmohan, Masilamani ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

Alkenes; Arylboronic acids; Michael addition; Mizoroki Heck addition; Nickel

Indexed keywords

EID: 35948994495     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700128     Document Type: Article

References (66)

1. a) Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), John Wiley & Sons, New York, 2002;
2. b) M. Kanai, M. Shibasaki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley, New York, 2000, p. 569;
3. c) A. Alexakis in Transition Metals for Organic Synthesis, Vol. 1 (Ed.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, chap. 3.10;
4. d) J. Tsuji, Palladium Reagents and Catalysts, John Wiley & Sons, Chichester, 1995;
5. e) B. H. Lipshutz in Organometattics in Synthesis (Ed.: M. Schlosser), Wiley, New York, 1994, pp. 283-382;
6. f) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis Pergamon, Oxford, 1992;
7. g) B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771.
8. a) W-L. Duan, H. Iwamura, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2007, 129, 2130;
9. b) T. Nishimura, S. Hirabayashi, Y. Yasuhara, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 2556;
10. c) G. Chen, N. Tokunaga, T. Hayashi, Org. Lett. 2005, 7, 2285;
11. d) R. Shintani, W.-L. Duan, T. Nagano, A. Okada, T. Hayashi, Angew. Chem. 2005, 117, 4687;
12. Angew. Chem. Int. Ed. 2005, 44, 4611;
13. e) N. Miyaura, Top. Curr. Chem. 2002, 219, 11.
14. a) F. Gini, B. Hessen, B. L. Feringa, A. J. Minnaard, Chem. Commun. 2007, 710;
15. b) T. Koike, X. Du, T. Sanada, Y. Danda, A. Mori, Angew. Chem. 2003, 115, 93;
16. Angew. Chem. Int. Ed. 2003, 42, 89;
17. c) S. Oi, Y. Honma, Y. Inoue, Org. Lett. 2002, 4, 667;
18. d) A. Mori, Y. Danda, T. Fujii, K. Hirabayashi, K. Osakada, J. Am. Chem. Soc. 2001, 123, 10774;
19. e) T.-S. Huang, C.-J. Li, Chem. Commun. 2001, 2348.
20. a) S. Oi, M. Moro, H. Ito, Y. Honma, S. Miyano, Y. Inoue, Tetrahedron 2002, 58, 91;
21. b) Y. Meng, C.-J. Li, J. Am. Chem. Soc. 2000, 122, 9538;
22. c) M. Ishigedani, T. Hayashi, J. Am. Chem. Soc. 2000, 122, 976;
23. d) K. Hirabayashi, J. Ando, Y. Nishihara, A. Mod, T. Hiyama, Synlett 1999, 99.
24. a) R. Shintani, T. Yamagami, T. Kimura, T. Hayashi, Org. Lett. 2005, 7, 5317;
25. b) R. Shintani, N. Tokunaga, H. Doi, T. Hayashi, J. Am. Chem. Soc. 2004, 126, 6240;
26. c) K. Soai, T. Hayasaka, S. Ugajin, J. Chem. Soc. Chem. Commun. 1989, 516.
27. a) S. T. Sarraf, J. L. Leighton, Org. Lett. 2000, 2, 3205;
28. b) S. Cacchi, D. Misiti, G. Palmieri, Tetrahedron 1981, 37, 2941;
29. c) R. C. Larock, J. C. Bernhardt, J. Org. Chem. 1977, 42, 1680.
30. a) N. Kudo, M. Perseghini, G. C. Fu, Angew. Chem. 2006, 118, 1304;
31. Angew. Chem. Int. Ed. 2006, 45, 1282;
32. b) C.-G. Dong, Q.-S. Hu, J. Am. Chem. Soc. 2005, 127, 10006;
33. c) S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633;
34. d) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
35. Pd: a) K. S. Yoo, C. H. Yoon, K. W. Jung, J. Am. Chem. Soc. 2006, 128, 16384, and references therein;
36. b) C. H. Yoon, K. S. Yoo, S. W. Yi, R. K. Mishra, K. W. Jung, Org. Lett. 2004, 6, 4037;
37. c) M.M.S. Andappan, P. Nilsson, M. Larhed, Chem. Commun. 2004, 218, and references therein;
38. d) G. W. Kabalka, S. K. Guchhait, A. Naravane, Tetrahedron Lett. 2004, 45, 4685;
39. e) Y. C. Jung, R. K. Mishra, C. H. Yoon, K. W. Jung, Org. Lett. 2003, 5, 2231;
40. f) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H.-F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313;
41. g) J. H. Delcamp, M. C. White, J. Am. Chem. Soc. 2006, 128, 15076; Rh:
42. h) G. D. L. Herran, C. Murcia, A. G. Csaky. Org. Lett. 2005, 7, 5629;
43. i) G. Zou, Z. Wang, J. Zhu, J. Tang. Chem. Commun. 2003, 2438;
44. j) M. Lautens, A. Roy, K. Fukuoka, K. Fagnou, B. Martin-Matute, J. Am. Chem. Soc. 2001, 123, 5358; Ru:
45. k) E. J. Farrington, J. M. Brown, C. F. J. Barnard, E. Roswell, Angew. Chem. 2002, 114, 177;
46. Angew. Chem. Int. Ed. 2002, 41, 161.
47. Pd: a) T. Nishikata, Y. Yamamoto, N. Miyaura, Angew. Chem. 2003, 115, 2874;
48. Angew. Chem. Int. Ed. 2003, 42, 2768;
49. b) T. Nishikata, Y. Yamamoto, N. Miyaura, Organometallics 2004, 23, 4317; Rh:
50. c) A. Kina, Y. Yasuhara, T. Nishimura, H. Iwamura, T. Hayashi, Chem. Asian J. 2006, 1, 707;
51. d) R. Shintani, T. Kiura, T. Hayashi, Chem. Commun. 2005, 3213;
52. e) R. Shintani, K. Okamoto, T. Hayashi, Org. Lett. 2005, 7, 4757;
53. f) Y. Otomaru, K. Okamoto, R. Shintani, T. Hayashi, J. Org. Chem. 2005, 70, 2503;
54. g) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169;
55. h) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829;
56. i) T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052;
57. j) S. Sakuma, M. Sakai, R. Itooka, N. Miyaura, J. Org. Chem. 2000, 65, 5951.
58. T. Jeffery in Advances in Metal-Organic Chemistry, Vol. 5 (Ed.: L. S. Liebeskind), JAI, Greenwich, 1996, p. 153.
59. G. A. Sough, R. G. Bergmann, C. H. Heathcock, J. Am. Chem. Soc. 1989, 111, 938.
60. a) K. Parthasarathy, M. Jeganmohan, C.-H. Cheng, Org. Lett. 2006, 8, 621;
61. b) M.-S. Wu, M. Jeganmohan, C.-H. Cheng, J. Org. Chem. 2005, 70, 9545;
62. c) M.-S. Wu, D.-K. Rayabarapu, C.-H. Cheng, J. Org. Chem. 2004, 69, 8407.
63. Nickel-catalyzed Heck reaction of aryl halides with activated alkenes: S. Ma, H. Wang, K. Gao, F. Zhao, J. Mol. Catal. A 2006, 248, 17, and references therein.
64. G. B. Smith, G. C. Dezeny, D. L. Hughes, A. O. King, T. R. Verhoeven, J. Org. Chem. 1994, 59, 8151.
65. a) M. J. Loots, J. Schwartz, J. Am. Chem. Soc. 1977, 99, 8045;
66. b) R. T. Hansen, D. B. Carr, J. Schwartz, J. Am. Chem. Soc. 1978, 100, 2244.