Gallium tribromide catalyzed coupling reaction of alkenyl ethers with ketene silyl acetals

Angewandte Chemie - International Edition

Volumn 51, Issue 32, 2012, Pages 8073-8076

  Nishimoto, Yoshihiro ^a   Ueda, Hiroki ^a   Yasuda, Makoto ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

alkenes; homogenous catalysis; indium; silicon; synthetic methods

Indexed keywords

ALKENYL ETHERS; ALKENYL GROUPS; CATALYZED COUPLING; HOMOGENOUS CATALYSIS; KETENE SILYL ACETAL; REACTION SYSTEM; SYNTHETIC METHODS;

CATALYSIS; INDIUM; OLEFINS; SILICON;

ORGANIC COMPOUNDS;

ACETAL DERIVATIVE; ALKENE; BROMIDE; ESTER; ETHER DERIVATIVE; ETHYLENE DERIVATIVE; GALLIUM; KETENE; KETONE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ACETALS; ALKENES; BROMIDES; CATALYSIS; ESTERS; ETHERS; ETHYLENES; GALLIUM; KETONES; MOLECULAR STRUCTURE; SILANES;

EID: 84864754987     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201203778     Document Type: Article

References (53)

1. Metal-Catalyzed Cross-Coupling Reactions, 2nd. ed., (Eds.: A. de Meijere, F. Diederich, Wiley-VCH, Weinheim, 2004
2. Comprehensive Organometallic Chemistry III, (Eds.:, R. H. Crabtree, D. M. P. Mingos,), Elsevier, Oxford, UK, 2007.
3. E. Wenkert, E. L. Michelotti, C. S. Swindell, J. Am. Chem. Soc. 1979, 101, 2246
4. E. Wenkert, E. L. Michelotti, C. S. Swindell, M. Tingoli, J. Org. Chem. 1984, 49, 4894
5. Y. Matsuura, M. Tamura, T. Kochi, M. Sato, N. Chatani, F. Kakiuchi, J. Am. Chem. Soc. 2007, 129, 9858
6. S. Zhu, G. Jin, H. Jiang, Can. J. Chem. 2005, 83, 2127
7. B. T. Guan, S. K. Xiang, T. Wu, Z. P. Sun, B. Q. Wang, K. Q. Zhaob, Z. J. Shi, Chem. Commun. 2008, 1437
8. T. Shimasaki, Y. Konno, M. Tobisu, N. Chatani, Org. Lett. 2009, 11, 4890
9. A. J. Brockway, M. González-Lõpez, J. C. Fettinger, J. T. Shaw, J. Org. Chem. 2011, 76, 3515.
10. J. Y. Yu, R. Kuwano, Angew. Chem. 2009, 121, 7353
11. Angew. Chem. Int. Ed. 2009, 48, 7217
12. H. W. Lee, F. Y. Kwong, Synlett 2009, 3151.
13. K. W. Quasdorf, X. Tian, N. K. Garg, J. Am. Chem. Soc. 2008, 130, 14422
14. B. J. Li, Y. Z. Li, X. Y. Lu, J. Liu, B. T. Guan, Z. J. Shi, Angew. Chem. 2008, 120, 10278
15. Angew. Chem. Int. Ed. 2008, 47, 10124
16. B. J. Li, L. Xu, Z. H. Wu, B. T. Guan, C. L. Sun, B. Q. Wang, Z. J. Shi, J. Am. Chem. Soc. 2009, 131, 14656.
17. F. H. Porée, A. Clavel, J. F. Betzer, A. Pancrazi, J. Ardisson, Tetrahedron Lett. 2003, 44, 7553.
18. A. S. E. Karlström, K. Itami, J. E. Bäckvall, J. Org. Chem. 1999, 64, 1745
19. Y. Nan, Z. Yang, Tetrahedron Lett. 1999, 40, 3321.
20. T. Hayashi, Y. Katsuro, M. Kumada, Tetrahedron Lett. 1980, 21, 3915.
21. Only the dimerization of silyl vinyl ethers was reported., C. Chen, R. F. Jordan, J. Am. Chem. Soc. 2010, 132, 10254.
22. X. Dai, N. A. Strotman, G. C. Fu, J. Am. Chem. Soc. 2008, 130, 3302
23. S. Lou, G. C. Fu, J. Am. Chem. Soc. 2010, 132, 5010. The α-alkenylation of aldehydes by SOMO activation
24. H. Kim, D. W. C. MacMillan, J. Am. Chem. Soc. 2008, 130, 398. Coupling reactions using alkenylbismuth(V) compounds
25. T. Ooi, R. Goto, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 10494
26. Y. Matano, H. Imahori, J. Org. Chem. 2004, 69, 5505. Coupling reactions using alkenyllead(IV) compounds
27. M. G. Moloney, J. T. Pinhey, J. Chem. Soc. Chem. Commun. 1984, 965
28. S. Hashimoto, Y. Miyazaki, T. Shinoda, S. Ikegami, Tetrahedron Lett. 1989, 30, 7195. The coupling reaction using alkenyliodonium salts
29. M. Ochiai, T. Shu, T. Nagaoka, Y. Kitagawa, J. Org. Chem. 1997, 62, 2130. Alkenylations of 1,3-dicarbonyl compounds with alkynes
30. M. Nakamura, K. Endo, E. Nakamura, J. Am. Chem. Soc. 2003, 125, 13002
31. M. Nakamura, K. Endo, E. Nakamura, Org. Lett. 2005, 7, 3279
32. K. Endo, T. Hatakeyama, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 2007, 129, 5264
33. T. Fujimoto, K. Endo, H. Tsuji, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 2008, 130, 4492
34. Y. Itoh, H. Tsuji, K. Yamagata, K. Endo, I. Tanaka, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 2008, 130, 17161; Pioneering examples of the coupling reaction using silyl enolates and alkynes
35. J. Drouin, M.-A. Boaventura, J.-M. Conia, J. Am. Chem. Soc. 1985, 107, 1726
36. K. Maeyama, N. Iwasawa, J. Am. Chem. Soc. 1998, 120, 1928
37. M. Yamaguchi, T. Tsukagoshi, M. Arisawa, J. Am. Chem. Soc. 1999, 121, 4074
38. M. Arisawa, K. Akamatsu, M. Yamaguchi, Org. Lett. 2001, 3, 789
39. K. Imamura, E. Yoshikawa, V. Gevorgyan, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 4081.
40. Y. Nishimoto, R. Moritoh, M. Yasuda, A. Baba, Angew. Chem. 2009, 121, 4647
41. Angew. Chem. Int. Ed. 2009, 48, 4577
42. Y. Nishimoto, H. Ueda, Y. Inamoto, M. Yasuda, A. Baba, Org. Lett. 2010, 12, 3390.
43. Y. Nishimoto, H. Ueda, M. Yasuda, A. Baba, Chem. Eur. J. 2011, 17, 11135.
44. Y. Nishimoto, M. Takeuchi, M. Yasuda, A. Baba, Angew. Chem. 2012, 124, 1075
45. Angew. Chem. Int. Ed. 2012, 51, 1051.
46. R. Amemiya, A. Fujii, M. Arisawa, M. Yamaguchi, J. Organomet. Chem. 2003, 686, 94
47. R. Amemiya, K. Suwa, J. Toriyama, Y. Nishimura, M. Yamaguchi, J. Am. Chem. Soc. 2005, 127, 8252
48. R. Amemiya, Y. Miyake, M. Yamaguchi, Tetrahedron Lett. 2006, 47, 1797
49. Y. Nishimura, R. Amemiya, M. Yamaguchi, Tetrahedron Lett. 2006, 47, 1839.
50. D. J. Ager, Synthesis 1984, 384
51. A. G. M. Barrett, J. M. Hill, E. M. Wallace, J. A. Flygare, Synlett 1991, 764
52. L. F. van Staden, D. Gravestock, D. J. Ager, Chem. Soc. Rev. 2002, 31, 195; β Eliminations from β-oxyalkylmetals. Peterson olefinations using β-hydroxymetals other than β-hydroxysilanes
53. D. J. Ager, Org. React. 1990, 38, 1.