Synthesis 2017; 49(11): 2495-2500
DOI: 10.1055/s-0036-1588726
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Free Double Silylation of 1,2-Dibromobenzenes Using a Mg/LiCl/DMI System

Tsugio Kitamura*
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan   Email: kitamura@cc.saga-u.ac.jp
,
Rin Yamada
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan   Email: kitamura@cc.saga-u.ac.jp
,
Keisuke Gondo
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan   Email: kitamura@cc.saga-u.ac.jp
,
Nobuo Eguchi
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan   Email: kitamura@cc.saga-u.ac.jp
,
Juzo Oyamada
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan   Email: kitamura@cc.saga-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 26 December 2016

Accepted after revision: 01 February 2017

Publication Date:
22 February 2017 (online)


Abstract

The reaction of 1,2-dibromobenzenes with chlorotrimethylsilane efficiently proceeded in the presence of Mg and LiCl in DMI under mild conditions, giving 1,2-bis(trimethylsilyl)benzenes in good to high yields. The reaction of 1,2-dibromobenzenes with chlorodimethylsilane under the same conditions afforded the corresponding 1,2-bis(dimethylsilyl)benzenes in high yields. Functional group transformations of 1,2-bis(trimethylsilyl)benzene were conducted to demonstrate the synthetic utility.

Supporting Information