4.8 Article

Rapid and Simple Access to alpha-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

Journal

ORGANIC LETTERS
Volume 24, Issue 2, Pages 786-790

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c04336

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Funding

  1. Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang [2019R01005]
  2. Taizhou University

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This study proposes a green alternative method using aqueous ammonia as the N source for the cyanating reagent, entirely avoiding the use of toxic cyanating reagents or metal catalysis.
A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reaction, aqueous ammonia offers a N source for the CN reagent and entirely avoids the use of toxic cyanating reagents or metal catalysis. Hence, we provide a green and alternative method for the synthesis of arylacetonitriles.

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