4.7 Article

Cyanotrifluoromethylthiolation of Unactivated Olefins through Intramolecular Cyano Migration

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 11, Pages 1959-1962

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700218

Keywords

Cyanation; trifluoromethylthiolation; alkenes; migration; radical reactions

Funding

  1. Soochow University
  2. National Natural Science Foundation of China [21402134, 21572148, 21272165]
  3. Natural Science Foundation of Jiangsu Province [BK20140306]
  4. Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)

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A new protocol for the elusive cyanotrifluoromethylthiolation of unactivated olefins is described. A broad range of vicinal CF3S-substituted alkyl nitriles are furnished in good yields under mild reaction conditions. The intramolecular cyano migration strategy is harnessed for the trifluoromethylthiolation of alkenes for the first time, thus offering an efficient tool for the construction of alkyl trifluoromethylthioethers.

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