A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides

作者: Norio Miyaura , Kinji Yamada , Akira Suzuki

DOI: 10.1016/S0040-4039(01)95429-2

关键词:

摘要: Abstract The representative (E)-1-alkenyldisiamylboranes and (E)-1-alkenyl-1, 3, 2-benzodioxaboroles readily obtainable via hydroboration of 1-alkynes react with 1-alkenyl halides or 1-alkynyl halides in the presence of a catalytic amount of tetrakis (triphenylphosphine) palladium and base to give corresponding conjugated (E)-dienes or (E)-enynes with high regio-and stereospecificity in good yields, respectively.

参考文章(11)
Harold A. Dieck, Richard F. Heck, Palladium-catalyzed conjugated diene synthesis from vinylic halides and olefinic compounds Journal of Organic Chemistry. ,vol. 40, pp. 1083- 1090 ,(1975) , 10.1021/JO00896A020
George M. Whitesides, Charles P. Casey, Jeanne K. Krieger, Thermal decomposition of vinylic copper(I) and silver(I) organometallic compounds Journal of the American Chemical Society. ,vol. 93, pp. 1379- 1389 ,(1971) , 10.1021/JA00735A011
George. Zweifel, Norman L. Polston, Charles C. Whitney, A stereoselective synthesis of conjugated dienes from alkynes via the hydroboration-iodination reaction Journal of the American Chemical Society. ,vol. 90, pp. 6243- 6245 ,(1968) , 10.1021/JA01024A068
Shigeru Baba, Eiichi Negishi, A novel stereospecific alkenyl-alkenyl cross-coupling by a palladium- or nickel-catalyzed reaction of alkenylalanes with alkenyl halides Journal of the American Chemical Society. ,vol. 98, pp. 6729- 6731 ,(1976) , 10.1021/JA00437A067
Richard C. Larock, Mercury in organic chemistry. 7. A convenient synthesis of symmetrical conjugated dienes and polyenes Journal of Organic Chemistry. ,vol. 41, pp. 2241- 2246 ,(1976) , 10.1021/JO00875A004
Yoshinori Yamamoto, Hidetaka Yatagai, Kazuhiro Maruyama, Akio Sonoda, Shunichi Murahashi, Reaction of alkenylboranes with methylcopper. A convenient new procedure for the synthesis of symmetrical (E,E)-1,3-dienes ChemInform. ,vol. 8, pp. 5652- 5656 ,(1977) , 10.1021/JA00459A021
D. R. Coulson, L. C. Satek, S. O. Grim, Tetrakis(triphenylphosphine)palladium(0) Inorganic Syntheses: Reagents for Transition Metal Complex and Organometallic Syntheses, Volume 28. pp. 121- 124 ,(2007) , 10.1002/9780470132449.CH23