4.8 Article

Co(OAc)2-Catalyzed Trifluoromethylation and C(3)-Selective Arylation of 2-(Propargylamino)pyridines via a 6-Endo-Dig Cyclization

Journal

ORGANIC LETTERS
Volume 19, Issue 22, Pages 6052-6055

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02759

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Funding

  1. program for the National Science Foundation of China [21738002, 21372073, 21572054, 21572055]
  2. Fundamental Research Funds for the Central Universities

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A Co(OAc)(2)-catalyzed trifluoromethylation and subsequent C(3) -selective arylation of 2-(propargylamino)-pyridines has been developed. A new 6-endo-dig cyclization involving an unprecedented C(3) selective arylation of the pyridines instead of a commonly observed 5-exo-dig cyclization with N is realized. Moreover, the study presents the first case of the installation of a trifluoromethyl group into electron deficient azaarenes. The process delivers an efficient cascade approach to new trifluoromethylated 1,8-naphthyridine structures with a broad substrate scope.

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