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Synlett 2009(13): 2198-2200  
DOI: 10.1055/s-0029-1217571
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Mizoroki-Heck-Type Reaction of Aryl Trimethoxysilanes

Zhishi Ye, Fan Chen, Fang Luo, Wenhui Wang, Baoda Lin, Xiaofei Jia, Jiang Cheng*
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China
Fax: +86(577)88156826; e-Mail: jiangcheng@wzu.edu.cn;
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Publication History

Received 24 April 2009
Publication Date:
16 July 2009 (online)

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Abstract

A palladium-catalyzed Mizoroki-Heck-type reaction ­of aryl trimethoxysilanes with olefins is described. A series of ­ArSi(OMe)3 and olefins, including electron-rich and electron-deficient analogues worked well in the procedure, affording the arylation products in moderate to good yields.

Key words

palladium-catalyzed - aryltrimethoxysilanes - cross-coupling - Heck reaction - alkenes

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General procedure: Under air, a reaction tube was charged with olefin (0.2 mmol), aryl trimethoxysilane (0.3 mmol), Pd(OAc)2 (2.2 mg, 5 mol%), 1,10-phenanthroline (3.6 mg, 10 mol%), AgF (76 mg, 0.6 mmol) and DMF (2 mL). The mixture was stirred at 60 ˚C. After completion of the reaction (monitored by TLC), EtOAc (20 mL) was added and the mixture was washed with water (10 × 3 mL). Then the organic layer was dried, concentrated in vacuo and the residue was purified by flash column chromatography on a silica gel to give the desired product.