Palladium-catalyzed silylene-1,3-diene [4 + 1] cycloaddition with use of (aminosilyl)boronic esters as synthetic equivalents of silylene

Journal of the American Chemical Society
Toshimichi OhmuraMichinori Suginome

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 (i.e., 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. Stereospecific ring formation took place in the reaction with either stereoisomer of 5,7-dodecadiene: the (E,E)-diene gave the cis product, whereas selective formation of the trans product was observed in the reaction of the isomeric (E,Z)-diene. The [4 + 1] cycloaddition followed by dehydrogenation with DDQ or chloranil afforded 2,4- and 2,5-diarylsiloles.

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Citations

Nov 21, 2012·Chemical Reviews·Martin OestreichMarius Mewald
Apr 23, 2011·Journal of the American Chemical Society·Kazuyuki OshimaMichinori Suginome
Oct 2, 2015·Inorganic Chemistry·Sabrina KhooCheuk-Wai So
Aug 14, 2015·The Journal of Organic Chemistry·Baosheng WeiZhenfeng Xi
Apr 20, 2017·Chemistry : a European Journal·Srimanta Manna, Andrey P Antonchick
Aug 6, 2010·Chemistry : a European Journal·Alexandre WelleOlivier Riant
Mar 21, 2012·Macromolecular Rapid Communications·Zujin ZhaoBen Zhong Tang
Nov 5, 2015·Angewandte Chemie·Alison E Wendlandt, Shannon S Stahl
Mar 6, 2019·Organic Letters·Toshimichi OhmuraMichinori Suginome

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