Palladium-Catalyzed Silylene-1, 3-Diene [4+ 1] Cycloaddition with Use of (Aminosilyl) boronic Esters as Synthetic Equivalents of Silylene

…, K Masuda, I Takase, M Suginome

Index: Ohmura, Toshimichi; Masuda, Kohei; Takase, Ichiro; Suginome, Michinori Journal of the American Chemical Society, 2009 , vol. 131, # 46 p. 16624 - 16625

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Citation Number: 35

Abstract

Silylboronic esters bearing a dialkylamino group on the silicon atoms reacted with 1, 3- dienes in the presence of a palladium catalyst to give silacyclopent-3-enes (ie, 2, 5- dihydrosiloles) in high yields via efficient silylene transfer from the silylboronic ester to the 1, 3-dienes. The [4+ 1] cycloaddition was applicable to the parent 1, 3-butadiene and various mono-, di-, and trisubstituted 1, 3-dienes having silyloxy, cyano, and ester groups. ...