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Copper-Mediated Cyanotrifluoromethylation of Styrenes Using the Togni Reagent

Nadia O. Ilchenko, Pär G. Janson and Kálmán J. Szabó*

*Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden, Email: kalmanorgan.su.se

N. O. Ilchenko, P. G. Janson, K. J. Szabó, J. Org. Chem., 2013, 78, 11087-11091.

DOI: 10.1021/jo401831t (free Supporting Information)


Abstract

A highly regioselective cyanotrifluoromethylation of electron-deficient styrenes with a trifluoromethylated hypervalent iodine reagent proceeds under mild conditions in the presence of a bulky phosphine and CuCN. The process involves the consecutive formation of two C-C bonds in a single addition reaction. In the presence of a p-methoxy substituent in the styrene, oxytrifluoromethylation occurs instead of the cyanotrifluoromethylation.

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Key Words

cyanation, trifluoromethylation, multicomponent reactions


ID: J42-Y2013