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J Org Chem. 2013 Nov 1;78(21):11087-91. doi: 10.1021/jo401831t. Epub 2013 Oct 11.

Copper-mediated cyanotrifluoromethylation of styrenes using the Togni reagent.

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1
Department of Organic Chemistry, Stockholm University , SE-106 91 Stockholm, Sweden.

Abstract

Styrenes with an electron-deficient double bond undergo cyanotrifluoromethylation with a trifluoromethylated hypervalent iodine reagent in the presence of CuCN. The reaction proceeds under mild conditions in the presence of bulky phosphines or B2pin2 additives. The process is highly regioselective and 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.

PMID:
24079395
DOI:
10.1021/jo401831t
[Indexed for MEDLINE]
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