Catalytic borylation and silylation of unsaturated organic molecules: Reaction control by transition metal catalysts and applications to organic synthesis

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 71, Issue 8, 2013, Pages 804-817

  Ohmura, Toshimichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Enantioselective synthesis; Oragano silicon compounds; Organoboron compounds; Regioselective synthesis; Silaboration; Stereoselective synthesis; Transition metal catalyzed reaction

Indexed keywords

ENANTIOSELECTIVE SYNTHESIS; ORAGANO-SILICON COMPOUNDS; ORGANOBORON COMPOUND; REGIOSELECTIVE SYNTHESIS; SILABORATION; STEREOSELECTIVE SYNTHESIS; TRANSITION-METAL-CATALYZED REACTIONS;

CATALYSIS; CATALYSTS; ENANTIOSELECTIVITY; ESTERIFICATION; ESTERS; HYDROCARBONS; LIGANDS; MOLECULES; PHOSPHORUS; PLATINUM; REGIOSELECTIVITY; SILICON; SILICON COMPOUNDS; STEREOCHEMISTRY; STEREOSELECTIVITY; TRANSITION METALS;

SYNTHESIS (CHEMICAL);

EID: 84890093027     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.71.804     Document Type: Review

References (59)

1. I. Beletskaya, C. Moberg, Chem. Rev., 99, 3435 (1999)
2. L.-B. Han, M. Tanaka, Chem. Commun., 395, 402 (1999)
3. S. Onozawa, M. Tanaka, J. Synth. Org. Chem., Jpn., 60, 826 (2002)
4. Y. Ito, J. Organomet. Chem., 576, 300 (1999)
5. M. Suginome, Y. Ito, Chem. Rev., 100, 3221 (2000)
6. I. Beletskaya, C. Moberg, Chem. Rev., 106, 2320 (2006)
7. M. Suginome, T. Matsuda, T. Ohmura, A. Seki, M. Murakami, In "Comprehensive Organometallic Chemistry III" eds. by R. H. Crabtree, D. M. P. Mingos, Vol. ed. by I. Ojima, Elsevier; Oxford, 2007; Vol. 10, p725
8. H. E. Burks, J. P. Morken, Chem. Commun., 2007, 4717
9. M. Suginome, J. Synth. Org. Chem., Jpn., 65, 1048 (2007)
10. T. Ohmura, M. Suginome, Bull. Chem. Soc. Jpn., 82, 29 (2009)
11. M. Suginome, T. Ohmura, In "Boronic Acids Second Edition" ed. by D. G. Hall, Wiley-VCH: 2011, Vol. 1, p 171
12. (1)M. Oestreich, E, Hartmann, M. Mewald, Chem. Rev., 113, 402 (2013)
13. T. Hayashi, Y. Matsumoto, Y. Ito, J. Am. Chem. Soc, 110, 3692 (1988)
14. M. Suginome, H. Nakamura, Y. Ito, Tetrahedron Lett., 38, 555 (1997)
15. T. B. Marder, N. C. Norman, C. R. Rice, Tetrahedron Lett., 39, 155 (1998)
16. W. Clegg, T. R. F. Johann, T. B. Marder, N. C. Norman, A. G. Orpen, T. M. Peakman, M. J. Quayle, C. R. Rice, A. J. Scott, J. Chem. Soc, Dalton Trans., 1998, 1431
17. S. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun., 1999, 1863
18. M. Suginome, Y. Ohmori, Y. Ito, Synlett, 1999, 1567
19. M. Suginome, Y. Ohmori, Y. Ito, J. Organomet. Chem., 611, 403 (2000)
20. M. Suginome, T. Ohmura, Y. Miyake, S. Mitani, Y. Ito, M. Murakami, J. Am. Chem. Soc, 125, 11174 (2003)
21. T. Ohmura, M. Suginome, Org Lett, 8, 2503 (2006)
22. T. Ohmura, H. Taniguchi, M. Suginome, J. Am. Chem. Soc, 128, 13682 (2006)
23. M. Suginome, T. Matsuda, Y. Ito, J. Am. Chem. Soc, 122, 11015 (2000)
24. T. Ohmura, H. Taniguchi, Y. Kondo, M. Suginome, J. Am. Chem. Soc, 129, 3518 (2007)
25. Y. Akai, T. Yamamoto, Y. Nagata, T. Ohmura, M. Suginome, J. Am. Chem. Soc, 134, 11092 (2012)
26. Y. Abe, K. Kuramoto, M. Ehara, H. Nakatsuji, M. Suginome, M. Murakami, Y. Ito, Organometallics, 27, 1736 (2008)
27. T. Ohmura, H. Taniguchi, M. Suginome, Org. Lett, 11, 2880 (2009)
28. M. Suginome, T. Matsuda, H. Nakamura, Y. Ito, Tetrahedron, 55, 8787 (1999)
29. M. Suginome, T. Matsuda, Y. Ito, Organometallics, 19, 4647 (2000)
30. T. Ohmura, K. Masuda, H. Furukawa, M. Suginome, Organometallics, 26, 1291 (2007)
31. M. Suginome, H. Nakamura, Y. Ito, Angew. Chem., Int. Ed. Engl, 36, 2516 (1997)
32. T. Ohmura, H. Furukawa, M. Suginome, J. Am. Chem. Soc, 128, 13366 (2006)
33. T. Ohmura, Y. Takasaki, H. Furukawa, M. Suginome, Angew. Chem. Int. Ed., 48, 2372 (2009)
34. M. Suginome, H. Nakamura, Y. Ito, Chem. Commun., 1996, 2777
35. S. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun., 1997, 1229
36. J. C. A. Da Silva, M. Birot, J.-P. Pillot, M. Pétraud, J. Organomet. Chem., 646, 179 (2002)
37. M. Suginome, H. Noguchi, T. Hasui, M. Murakami, Bull. Chem. Soc. Jpn., 78, 323 (2005)
38. T. Ohmura, K. Masuda, M. Suginome, J. Am. Chem. Soc, 130, 1526 (2008)
39. T. Ohmura, K. Oshima, M. Suginome, Chem. Commun., 2008, 1416
40. T. Ohmura, K. Oshima, H. Taniguchi, M. Suginome, J. Am. Chem. Soc, 132, 12194 (2010)
41. T. Ohmura, K. Oshima, M. Suginome, Angew. Chem. Int. Ed., 50, 12501 (2011)
42. M. Tanabe, J. Jiang, H. Yamazawa, K. Osakada, T. Ohmura, M. Suginome, Organometallics, 30, 3981 (2011)
43. T. Ohmura, K. Masuda, I. Takase, M. Suginome, J. Am. Chem. Soc, 131, 16624 (2009)
44. K. L. Bobbitt, P. P. Gaspar, J. Organomet. Chem., 499, 17 (1995)
45. R.-J. Hwang, R. T. Conlin, P. P. Gaspar, J. Organomet. Chem., 94, 038 (1975)
46. P. P. Gaspar, R.-J. Hwang, J. Am. Chem. Soc, 96, 6198 (1974)
47. R. T. Conlin, L. L. Peterson, J. Organomet. Chem., 232, 071 (1982)
48. D. Lei, R.-J. Hwang, P. P. Gaspar, J. Organomet. Chem., 271, 1 (1984)
49. K. Masuda, T. Ohmura, M. Suginome, Organometallics, 30, 1322 (2011)
50. (a)T. S. Hamilton, R. Adams, J. Am. Chem. Soc, 50, 2260 (1928)
51. N. C. Cook, J. E. Lyons, J. Am. Chem. Soc, 88, 3396 (1966)
52. L. Hao, J. F. Harrod, A.-M. Lebuis, Y. Mu, R. Shu, E. Samuel, H.-G. Woo, Angew. Chem. Int. Ed., 37, 3126 (1998)
53. J. F. Harrod, R. Shu, H. G. Woo, E. Samuel, Can. J. Chem., 79, 1075 (2001)
54. D. V. Gutsulyak, A. van der Est, G. I. Nikonov, Angew. Chem. Int. Ed., 50, 1384 (2011)
55. K. Oshima, T. Ohmura, M. Suginome, J. Am. Chem. Soc, 133, 7324 (2011)
56. A. Ariafard, E. S. Tabatabaie, A. T. Monfared, S. H. A. Assar, C. J. T. Hyland, B. F. Yates, Organometallics, 31, 1680 (2012)
57. K. Oshima, T. Ohmura, M. Suginome, J. Am. Chem. Soc, 134, 3699 (2012)
58. M. Arrowsmith, M. S. Hill, T. Hadlington, G. Kociok-Köhn, C. Weetman, Organometallics, 30, 5556 (2011)
59. K. Oshima, T. Ohmura, M. Suginome, Chem. Commun., 48, 8571 (2012)