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Synthesis of Tertiary Benzylic Nitriles via Nickel-Catalyzed Markovnikov Hydrocyanation of α-Substituted Styrenes

Yidan Xing, Rongrong Yu, Xianjie Fang

2020Organic Letters28 citationsDOI

Abstract

The Markovnikov hydrocyanation of α-substituted styrenes enables the synthesis of tertiary benzylic nitriles under nickel catalysis. The Lewis-acid-free transformation features an unprecedented functional groups tolerance, including the −OH and −NH2 groups. A broad range of tertiary benzylic nitriles were obtained in good to excellent yields. In addition, an asymmetric version of this reaction was preliminarily investigated.

Topics & Concepts

HydrocyanationChemistryMarkovnikov's ruleCatalysisNickelNitrileOrganic chemistryFunctional groupLewis acids and basesCombinatorial chemistryRegioselectivityPolymerCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions
Synthesis of Tertiary Benzylic Nitriles via Nickel-Catalyzed Markovnikov Hydrocyanation of α-Substituted Styrenes | Litcius