Synlett
DOI: 10.1055/s-0036-1590835
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© Georg Thieme Verlag Stuttgart · New York

Formal Nucleophilic Silyl Substitution of Aryl Halides with Silyllithium Reagents via Halogenophilic Attack of Silyl Nucleophiles

Eiji Yamamoto, Satoshi Ukigai, Hajime Ito*
  • Division of Applied Chemistry & Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan   Email: hajito@eng.hokudai.ac.jp
This work was financially supported by the NEXT (Japan) program (Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions) of Hokkaido University. This work was also supported by JSPS KAKENHI Grant Numbers 15H03804, 15K13633, and 26·2447. E.Y. was supported by a Grant-in-Aid for JSPS Fellows.
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Publication History

Received: 09 May 2017

Accepted after revision: 20 June 2017

Publication Date:
24 July 2017 (eFirst)

Published as part of the Cluster Silicon in Synthesis and Catalysis

Abstract

A new reaction has been developed for the formal nucleo­philic silyl substitution of aryl halides with silyllithium or silylpotassium reagents. Dimethylphenylsilyllithium reacted with various aryl halides to form the corresponding arylsilanes in moderate to good yields with concomitant formation of the disilanes under the optimized reaction conditions. Mechanistic studies indicated that this silyl substitution reaction progresses through polar halogenophilic attack of silyl nucleo­philes.

Supporting Information