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Nickel-Catalyzed Multicomponent Carbodifluoroalkylation of Electron-Deficient Alkenes

Na Rao, Yunze Li, Yun‐Cheng Luo, Yanxia Zhang, Xingang Zhang

2023ACS Catalysis62 citationsDOI

Abstract

The nickel-catalyzed multicomponent dicarbofunctionalization of alkenes represents one of the most straightforward approaches to complex organofluorine compounds. However, the catalytic carbofluoroalkylation of electron-deficient alkenes remains underdeveloped. Here, we report a nickel-catalyzed three-component aryldifluoroalkylation of industry-relevant acrylonitrile and acrylate with arylboronic acids and difluoroalkyl halides. The reaction can extend to a four-component nickel-catalyzed carbonylation reaction under 1 atm CO gas. This modular catalytic synthesis features synthetic convenience, high functional group tolerance, and simple components to construct complex difluoroalkylated compounds expediently. The synthetic utility has also been demonstrated by the diversified transformations of the resulting products into medicinal interest fluorinated compounds.

Topics & Concepts

CatalysisNickelChemistryAcrylonitrileCarbonylationCombinatorial chemistryHalideAlkeneOrganic chemistryCarbon monoxideCopolymerPolymerFluorine in Organic ChemistryCarbon dioxide utilization in catalysisCatalytic C–H Functionalization Methods
Nickel-Catalyzed Multicomponent Carbodifluoroalkylation of Electron-Deficient Alkenes | Litcius