Selective synthesis of multisubstituted olefins utilizing gem - And vic -diborylated vinylsilanes prepared by silylborylation of an alkynylboronate and diborylation of alkynylsilanes

Journal of Organic Chemistry

Volumn 79, Issue 1, 2014, Pages 285-295

  Jiao, Jiao ^a   Hyodo, Keita ^a   Hu, Hao ^a   Nakajima, Kiyohiko ^c   Nishihara, Yasushi ^a,b  

^a OKAYAMA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c AICHI UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVE; SELECTIVE SYNTHESIS; SUZUKI-MIYAURA CROSS-COUPLING REACTION; SYNTHETIC METHODS; VINYL SILANE;

CHEMISTRY; ORGANIC COMPOUNDS;

OLEFINS;

ALKENE; BORONIC ACID DERIVATIVE; IODIDE; IODOBENZENE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; DESILYLATION; ISOMER; PRECURSOR; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 84891670992     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4024057     Document Type: Article

References (87)

1. Negishi, E.; Abramovitch, A. Tetrahedron Lett. 1977, 18, 411
2. Flynn, A. B.; Ogilvie, W. W. Chem. Rev. 2007, 107, 4698
3. Negishi, E.; Huang, Z.; Wang, G.; Mohan, S.; Wang, C.; Hattori, H. Acc. Chem. Res. 2008, 41, 1474
4. Andrei, D.; Wnuk, S. F. J. Org. Chem. 2006, 71, 405
5. Jin, W.; Du, W.; Yang, Q.; Yu, H.; Chen, J.; Yu, Z. Org. Lett. 2011, 13, 4272
6. Yu, T.; Wu, X.; Yang, J. Chin. J. Chem. 2012, 30, 2798
7. Wencel-Delord, J.; Nimphius, C.; Patureau, F. W.; Glorius, F. Chem.-Asian J. 2012, 7, 1208
8. Aoyama, T.; Koda, S.; Takeyoshi, Y.; Ito, T.; Takido, T.; Kodomari, M. Chem. Commun. 2013, 49, 6605
9. Konno, T.; Kinugawa, R.; Morigaki, A.; Ishihara, T. J. Org. Chem. 2009, 74, 8456
10. Unsinn, A.; Dunst, C.; Knochel, P. Beilstein J. Org. Chem. 2012, 8, 2202
11. Yoshida, H.; Kageyuki, I.; Takaki, K. Org. Lett. 2013, 15, 952
12. Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840
13. Shindo, M.; Mori, S. Synlett 2008, 2231
14. Wang, T.; Hu, Y.; Zhang, S. Org. Biomol. Chem. 2010, 8, 2312
15. Shindo, M. Top. Curr. Chem. 2012, 327, 1
16. Stewart, I. C.; Ung, T.; Pletnev, A. A.; Berlin, J. M.; Grubbs, R. H.; Schrodi, Y. Org. Lett. 2007, 9, 1589
17. Rost, D.; Porta, M.; Gessler, S.; Blechert, S. A. Tetrahedron Lett. 2008, 49, 5968
18. Stenne, B.; Timperio, J.; Savoie, J.; Dudding, T.; Collins, S. K. Org. Lett. 2010, 12, 2032
19. Paek, S.-M. Molecules 2012, 17, 3348
20. Wang, Y.; Fordyce, E. A. F.; Chen, F.-Y.; Lam, H. W. Angew. Chem., Int. Ed. 2008, 47, 7350
21. Matsumoto, K.; Shindo, M. Adv. Synth. Catal. 2012, 354, 642
22. Aziz, J.; Brachet, E.; Hamze, A.; Peyrat, J.-F.; Bernadat, G.; Morvan, E.; Bignon, J.; Wdzieczak-Bakala, J.; Desravines, D.; Dubois, J.; Tueni, M.; Yassine, A.; Briona, J.-D.; Alami, M. Org. Biomol. Chem. 2013, 11, 430
23. Barczak, N. T.; Rooke, D. A.; Menard, Z. A.; Ferreira, E. M. Angew. Chem., Int. Ed. 2013, 52, 7579
24. Migita, A.; Shichijo, Y.; Oguri, H.; Watanabe, M.; Tokiwano, T.; Oikawa, H. Tetrahedron Lett. 2008, 49, 1021
25. Tran, V.; Minehan, T. G. Org. Lett. 2012, 14, 6100
26. Görmen, M.; Pigeon, P.; Top, S.; Hillard, E. A.; Huché, M.; Hartinger, C. G.; Montigny, F.; Plamont, M.-A.; Vessières, A.; Jaouen, G. ChemMedChem 2010, 5, 2039
27. Koh, M.; Park, S. B. Mol. Diversity 2011, 15, 69
28. Oliveira, A. C.; Hillard, E. A.; Pigeon, P.; Rocha, D. D.; Rodrigues, F. A. R.; Montenegro, R. C.; Costa-Lotufo, L. V.; Goulart, M. O. F.; Jaouen, G. Eur. J. Med. Chem. 2011, 46, 3778
29. Banerjee, M.; Emond, S. J.; Lindeman, S. V.; Rathore, R. J. Org. Chem. 2007, 72, 8054
30. Navale, T. S.; Thakur, K.; Rathore, R. Org. Lett. 2011, 13, 1634
31. Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577-11585
32. Kamei, T.; Itami, K.; Yoshida, J. Adv. Synth. Catal. 2004, 346, 1824
33. He, Z.; Kirchberg, S.; Fröhlich, R.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 3699
34. Schultz, A.; Diele, S.; Laschat, S.; Nimtz, M. Adv. Funct. Mater. 2001, 11, 441
35. Verkerk, U.; Fujita, M.; Dzwiniel, T. L.; McDonald, R.; Stryker, J. M. J. Am. Chem. Soc. 2002, 124, 998
36. Zhou, C.; Larock, R. C. J. Org. Chem. 2005, 70, 3765
37. Tsuji, H.; Ueda, Y.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2010, 132, 11854
38. Itami, K.; Mineno, M.; Muraoka, N.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 11778
39. Itami, K.; Yoshida, J. Bull. Chem. Soc. Jpn. 2006, 79, 811
40. Itami, K.; Yoshida, J. Chem.-Eur. J. 2006, 12, 3966
41. Nishihara, Y.; Miyasaka, M.; Okamoto, M.; Takahashi, H.; Inoue, E.; Tanemura, K.; Takagi, K. J. Am. Chem. Soc. 2007, 129, 12634
42. Nishihara, Y.; Saito, D.; Tanemura, K.; Noyori, S.; Takagi, K. Org. Lett. 2009, 11, 3546
43. Nishihara, Y.; Okada, Y.; Jiao, J.; Suetsugu, M.; Lan, M.-T.; Kinoshita, M.; Iwasaki, M.; Takagi, K. Angew. Chem., Int. Ed. 2011, 50, 8660
44. Nishihara, Y.; Suetsugu, M.; Saito, D.; Kinoshita, M.; Iwasaki, M. Org. Lett. 2013, 15, 2418
45. Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435
46. Han, L. B.; Tanaka, M. Chem. Commun. 1999, 395
47. Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067
48. Suginome, M.; Ito, Y. Chem. Rev. 2000, 100, 3221
49. Beletskaya, I.; Moberg, C. Chem. Rev. 2006, 106, 2320
50. Suginome, M.; Ito, Y. J. Organomet. Chem. 2003, 685, 218
51. Yoshida, H.; Nakano, S.; Mukae, M.; Ohshita, J. Org. Lett. 2008, 10, 4319
52. Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392
53. Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271
54. Iwadate, N.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 2548
55. Takaya, J.; Iwasawa, N. ACS Catal. 2012, 2, 1993
56. Ito, Y. J. Organomet. Chem. 1999, 576, 300
57. Suginome, M.; Ito, Y. J. Organomet. Chem. 2003, 680, 43
58. Oestreich, M.; Hartmann, E.; Mewald, M. Chem. Rev. 2013, 113, 402
59. Suginome, M.; Nakamura, H.; Ito, Y. Chem. Commun. 1996, 2777
60. Suginome, M.; Matsuda, T.; Ito, Y. Organometallics 1998, 17, 5233
61. Suginome, M.; Matsuda, T.; Nakamura, H.; Ito, Y. Tetrahedron 1999, 55, 8787
62. Ohmura, T.; Oshima, K.; Suginome, M. Chem. Commun. 2008, 1416
63. Ohmura, T.; Oshima, K.; Taniguchi, H.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 12194
64. Ohmura, T.; Oshima, K.; Suginome, M. Angew. Chem., Int. Ed. 2011, 50, 12501
65. Shimizu, M.; Nakamaki, C.; Shimono, K.; Schelper, M.; Kurahashi, T.; Hiyama, T. J. Am. Chem. Soc. 2005, 127, 12506
66. Shimizu, M.; Shimono, K.; Schelper, M.; Hiyama, T. Synlett 2007, 1969
67. Shimizu, M.; Hiyama, T. Proc. Jpn. Acad., Ser. B 2008, 84, 75
68. Shimizu, M.; Nagao, I.; Tomioka, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2008, 47, 8096
69. For a preliminary communication, see: Jiao, J.; Nakajima, K.; Nishihara, Y. Org. Lett. 2013, 15, 3294
70. Matteson, D. S.; Tripathy, P. B. J. Organomet. Chem. 1974, 69, 53
71. Hata, T.; Kitagawa, H.; Masai, H.; Kurahashi, T.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2001, 40, 790
72. Kurahashi, T.; Hata, T.; Masai, H.; Kitagawa, H.; Shimizu, M.; Hiyama, T. Tetrahedron 2002, 58, 6381
73. Miyaura, N. Top. Curr. Chem. 2002, 219, 11
74. Zhang, H.; Wei, J.; Zhao, F.; Liang, Y.; Wang, Z.; Xi, Z. Chem. Commun. 2010, 46, 7439
75. O'Brien, C. J.; Kantchev, E. A. B.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Chem.-Eur. J. 2006, 12, 4743
76. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158
77. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018
78. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley and Sons: New York, 1994; p 696.
79. Kitching, W.; Olszowy, H. A.; Drew, G. M.; Adcock, W. J. Org. Chem. 1982, 47, 5153
80. Brown, S. D.; Armstrong, R. W. J. Org. Chem. 1997, 62, 7076
81. Nakajima, R.; Delas, C.; Takayama, Y.; Sato, F. Angew. Chem., Int. Ed. 2002, 41, 3023
82. Yamago, S.; Fujita, K.; Miyoshi, M.; Kotani, M.; Yoshida, J. Org. Lett. 2005, 7, 909
83. Pilzak, G. S.; Lagen, B. V.; Hendrikx, C. C. J.; Sudhölter, E. J. R.; Zuilhof, H. Chem.-Eur. J. 2008, 14, 7939
84. Aikawa, K.; Hioki, Y.; Mikami, K. J. Am. Chem. Soc. 2009, 131, 13922
85. Cann, R. O.; Waltermire, R. E.; Chung, J.; Oberholzer, M.; Kasparec, J.; Ye, Y. K.; Wethman, R. Org. Process Res. Dev. 2010, 14, 1147
86. Gao, L.; Lu, J.; Song, Z.; Lin, X.; Xu, Y.; Yin, Z. Chem. Commun. 2013, 49, 8961
87. Miller, R. B.; Al-Hassan, M. I. J. Org. Chem. 1985, 50, 2121