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First Catalytic and Green Synthesis of Aryl-(Z)-vinyl Chlorides and Its Plausible Addition-Elimination Mechanism

Weike Su* and Can Jin

*College of Pharmaceutical Sciences, Zhejiang University of Technology, Zhejiang Key Laboratory of Pharmaceutical Engineering, Hangzhou 310014, PRC, Email: suweikezjut.edu.cn

W. Su, C. Jin, Org. Lett., 2007, 9, 993-996.

DOI: 10.1021/ol062991c (free Supporting Information)


Abstract

The reaction of aromatic ketones with bis(trichloromethyl) carbonate afforded aryl-(Z)-vinyl chlorides in the presence of scandium triflate, DMF, and benzoyl chloride as catalysts. A plausible addition-elimination mechanism is proposed. This catalytic method enables a green route to aryl-(Z)-vinyl chlorides.

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proposed catalytic cycle



Key Words

Chlorination, Elimination, Green Chemistry


ID: J54-Y2007-0840