Synthesis of 1,2-bis(trimethylsilyl)benzene derivatives from 1,2-dichlorobenzenes using a hybrid metal Mg/CuCl in the presence of LiCl in 1,3-dimethyl-2-imidazolidinone

Tsugio Kitamura; Keisuke Gondo; Toshimasa Katagiri

doi:10.1021/jo4000866

Synthesis of 1,2-bis(trimethylsilyl)benzene derivatives from 1,2-dichlorobenzenes using a hybrid metal Mg/CuCl in the presence of LiCl in 1,3-dimethyl-2-imidazolidinone

J Org Chem. 2013 Apr 5;78(7):3421-4. doi: 10.1021/jo4000866. Epub 2013 Mar 18.

Authors

Tsugio Kitamura¹, Keisuke Gondo, Toshimasa Katagiri

Affiliation

¹ Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan. kitamura@cc.saga-u.ac.jp

PMID: 23506000
DOI: 10.1021/jo4000866

Abstract

A practical and safe synthesis of 1,2-bis(trimethylsilyl)benzene from 1,2-dichlorobenzene and Me3SiCl was achieved by use of a hybrid metal of Mg and CuCl in the presence of LiCl in 1,3-dimethyl-2-imidazolidinone (DMI). This method does not require a toxic HMPA, provides a high yield of the product under mild conditions, and is also applied to synthesis of substituted 1,2-bis(trimethylsilyl)benzenes and poly(trimethylsilyl)benzenes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzene Derivatives / chemical synthesis*
Benzene Derivatives / chemistry
Copper / chemistry*
Imidazoles / chemistry*
Lithium Chloride / chemistry*
Magnesium / chemistry*
Molecular Structure

Substances

Benzene Derivatives
Imidazoles
1,3-dimethyl-2-imidazolidinone
Copper
Lithium Chloride
Magnesium
cupric chloride