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Synfacts 2007(5): 0497-0497  
DOI: 10.1055/s-2007-968445
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Catalytic Synthesis of (Z)-Vinyl Chlorides from Ketones

Contributor(s): Mark Lautens, Frédéric Ménard
W. Su*, C. Jin
Zhejiang University of Technology, Hangzhou, P. R. of China
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

General methods to prepare vinyl chlorides are of interest because of their increasing use as coupling partners in Pd-catalyzed reactions. A catalytic method was developed for the catalytic ipso chlorination and dehydration of various ketones. In the presence of a Lewis acid, the stereoselective formation of the (Z)-vinyl chlorides 3 was observed. Bis(trichloromethyl) carbonate (BTC, 2) was used as a safer alternative to other chlorinating reagents such as: phosgene, SOCl2, PCl3, POCl3, PCl5.