Synthesis 2010(12): 2005-2010  
DOI: 10.1055/s-0029-1218759
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(II)-Catalyzed Esterification of Arenecarboxylic Acids with Aryl- and Vinyl-Substituted Trimethoxysilanes

Fang Luoa, Changduo Panb, Pengcheng Qiana, Jiang Cheng*a
a College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325000, P. R. of China
Fax: +86(577)56998939; e-Mail: jiangcheng@wzu.edu.cn;
b Wenzhou Institute of Industry & Science, Wenzhou 325000, P. R. of China
Further Information

Publication History

Received 24 February 2010
Publication Date:
29 April 2010 (online)

Abstract

In this paper, the copper(II)-catalyzed esterification reaction of arenecarboxylic acids with aryl- or vinyl-substituted trimethoxysilanes is described. A series of aryltrimethoxysilanes and arenecarboxylic acids worked well under this procedure, affording aryl benzoate derivatives in moderate to good yields. Notably, trimethoxy(vinyl)silanes also worked well under this procedure giving a facile and versatile method to access vinyl benzoate derivatives.

18

For the transfer of phenyl from trimethoxy(phenyl)silane to copper(II), see refs 11c-e.

19

The formation of a Ag(0) film was observed. We reasoned that Cu(0) is produced after reductive elimination and is then oxidized to Cu(II) by Ag(I).