Facile Synthesis of Diverse 2,6-Disubstituted Arylsilanes via Silylamination and Silylsulfanylation of Aryne Intermediates Generated from o-Iodoaryl Triflates

A facile approach for preparing diverse 2,6-disubstituted arylsilanes is reported. Bisfunctionalization such as silylamination and silylsulfanylation of aryne intermediates was efficiently achieved by treating o-iodoaryl triflates with a silylmethyl Grignard reagent in the presence of N-silylamines...

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Bibliographic Details
Published in:Chemistry letters 2019-11, Vol.48 (11), p.1296-1299
Main Authors: Nakamura, Yu, Ozawa, Saki, Yoshida, Suguru, Hosoya, Takamitsu
Format: Article
Language:English
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Summary:A facile approach for preparing diverse 2,6-disubstituted arylsilanes is reported. Bisfunctionalization such as silylamination and silylsulfanylation of aryne intermediates was efficiently achieved by treating o-iodoaryl triflates with a silylmethyl Grignard reagent in the presence of N-silylamines or S-silyl sulfide, which afforded the corresponding arylsilanes, leaving a broad range of functional groups intact. A simplified procedure using non-silylated amines or a sulfide with chlorosilanes or a silyl triflate allowed the preparation of the desired arylsilanes via a three-component coupling approach, enhancing the convenience of the method.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.190573