Copper-Catalyzed Reagent-Controlled Regioselective Cyanoborylation of Vinylarenes
Shi-Jiang He1, Bing Wang1, Xi Lu1
1Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM , University of Science and Technology of China , Hefei 230026 , China.
Abstract:
A copper-catalyzed borylation/benzylic cyanation of vinylarenes whose regioselectivity is seemly common but scarcely achieved is reported. This unprecedented regioselectivity is realized through a structure-distinctive cyanating reagent, dimethylmalononitrile. This reaction can be applied to both π-extended and simple vinylarenes with various diboron reagents, and it exhibits good functional group compatibility. With the ample transformations of cyano and boronate groups, this reaction provides expedient access to complex organic structures.
Related Concept Videos
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Regioselectivity of Electrophilic Additions-Peroxide Effect
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Regioselective Formation of Enolates
EDTA: Auxiliary Complexing Reagents
Acid-Catalyzed Ring-Opening of Epoxides


