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Enantioselective Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes via Radical Process

Fei Wang, Dinghai Wang, Xiaolong Wan, Lianqian Wu, Pinhong Chen and Guosheng Liu*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, China, 200032, Email: gliumail.sioc.ac.cn

F. Wang, D. Wang, X. Wan, L. Wu, P. Chen, G. Liu, J. Am. Chem. Soc., 2016, 138, 15547-15550.

DOI: 10.1021/jacs.6b10468 (free Supporting Information)



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Abstract

A copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes provides various CF3-containing alkylnitriles with excellent enantiomeric excess. The reaction is initiated by a SET process between activated Togni’s CF3+ reagent and a Cu(I) catalyst. The released CF3 radical readily added to styrene to provide a benzylic radical, which is then trapped by a chiral Cu(II) cyanide species.

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Key Words

cyanation, trifluoromethylation


ID: J48-Y2016