4.8 Article

TfNHNHBoc as a Trifluoromethylating Agent for Vicinal Difunctionalization of Terminal Alkenes

Journal

ORGANIC LETTERS
Volume 18, Issue 15, Pages 3850-3853

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01862

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Funding

  1. National Natural Science Foundation of China [21472178, 21232007]
  2. National Key Basic Research Program of China [2014CB931800]

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An unprecedented application of trifluoromethanesulfonyl hydrazides as trifluoromethylating agents has been demonstrated in two vicinal difunctionalization reactions of terminal alkenes: the copper-catalyzed three-component vicinal chlorotrifluoromethylation of arylakenes with TfNHNHBoc and NaCl and the tandem trifluorornethylation/cyclization of N-arylacrylamides with TfNHNHBoc. The reactions, proceeded in the presence of inexpensive oxidants under mild conditions and provided a range of structurally diverse trifluoromethyl-containing compounds with high regioselectivity.

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