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Diisobutylaluminum Hydride Promoted Cyclization of 1-Hydrosilyl-4-silyl-1,3-enynes to Polysubstituted Siloles.
Title Diisobutylaluminum Hydride Promoted Cyclization of 1-Hydrosilyl-4-silyl-1,3-enynes to Polysubstituted Siloles.
Authors Kinoshita, H.; Ueda, A.; Fukumoto, H.; Miura, K.
Journal Org Lett
DOI 10.1021/acs.orglett.7b00038
Abstract

An efficient method for preparing unsymmetrically multisubstituted siloles is described. The reaction of 1-hydrosilyl-4-silyl-1,3-enynes with diisobutylaluminum hydride (DIBAL-H) gave multisubstituted siloles in good to high yields. This method could be applied to the synthesis of benzosiloles using 2-hydrosilyl-1-(silylethynyl)benzenes as substrates. The silole formation was also promoted even by a substoichiometric amount of DIBAL-H. The reaction provides a straightforward method to prepare siloles and benzosiloles.