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Catalytic Synthesis of (Z)-Vinyl Chlorides from Ketones
W. Su*, C. Jin
Zhejiang University of Technology, Hangzhou, P. R. of China
24 April 2007 (online)
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.