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. 2021 Aug 20;23(16):6466-6470.
doi: 10.1021/acs.orglett.1c02270. Epub 2021 Aug 3.

Ni-Catalyzed Reductive Arylcyanation of Alkenes

Ni-Catalyzed Reductive Arylcyanation of Alkenes

Hengxu Li et al. Org Lett. .

Abstract

We disclose a Ni-catalyzed reductive arylcyanation of alkene using environmentally benign and nontoxic organo cyanating reagent N-cyano-N-phenyl-p-toluenesulfonamide. This reaction provides a new method for the rapid synthesis of cyano-substituted oxindoles and isoquinoline-1,3-diones and features high functional group tolerance. In addition, an enantioselective version was developed for the construction of enantiomerically enriched 3-cyanomethyl oxindole. This method has also been applied to the synthesis of natural alkaloids (+)-esermethole and (+)-physostigmine.

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