4.7 Article

Trifluoromethyl radical triggered radical cyclization of N-benzoyl ynamides leading to isoindolinones

Journal

SCIENCE CHINA-CHEMISTRY
Volume 62, Issue 11, Pages 1542-1546

Publisher

SCIENCE PRESS
DOI: 10.1007/s11426-019-9627-x

Keywords

ynamides; trifluoromethylation; photocatalysis; cascade reactions; tandem processes; isoindolinones; modeling

Funding

  1. Sorbonne Universite, CNRS
  2. Servier

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Under photocatalytic reductive conditions, trifluoromethyl radical addition onto an ynamide followed by cyclization on a benzoyl moiety produces diverse isoindolinone platforms with good yields. The selectivity of the radical cyclization, N-benzoyl vs. N-benzyl as radical acceptor and the E/Z ratio of isomers have been rationalized by modeling.

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