Copper- and Iron-Catalyzed Decarboxylative Tri- and Difluoromethylation of α,β-Unsaturated Carboxylic Acids with CF₃SO₂Na and (CF₂HSO₂)₂Zn via a Radical Process

Zejiang Li, Zili Cui and Zhong-Quan Liu*

*State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou Gansu 730000, P. R. China, Email: liuzhqlzu.edu.cn

Z. Li, Z. Cui, Z.-Q. Liu, Org. Lett., 2013, 15, 406-409.

DOI: 10.1021/ol3034059

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Abstract

A copper-catalyzed decarboxylative trifluoromethylation of various α,β-unsaturated carboxylic acids was achieved by using a stable and inexpensive solid, sodium trifluoromethanesulfinate (CF₃SO₂Na, Langlois reagent). In addition, an iron-catalysis enables a difluoromethylation of aryl-substituted acrylic acids by using zinc difluoromethanesulfinate (DFMS, (CF₂HSO₂)₂Zn, Baran reagent) via a similar radical process.

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Key Words

trifluoromethylation, TBHP

ID: J54-Y2013-0240

Copper- and Iron-Catalyzed Decarboxylative Tri- and Difluoromethylation of α,β-Unsaturated Carboxylic Acids with CF3SO2Na and (CF2HSO2)2Zn via a Radical Process

Zejiang Li, Zili Cui and Zhong-Quan Liu*

Copper- and Iron-Catalyzed Decarboxylative Tri- and Difluoromethylation of α,β-Unsaturated Carboxylic Acids with CF₃SO₂Na and (CF₂HSO₂)₂Zn via a Radical Process