Nickel-Catalyzed Multicomponent Carbodifluoroalkylation of Electron-Deficient Alkenes

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 thr...

Full description

Saved in:
Bibliographic Details
Published in:ACS catalysis 2023-04, Vol.13 (7), p.4111-4119
Main Authors: Rao, Na, Li, Yun-Ze, Luo, Yun-Cheng, Zhang, Yanxia, Zhang, Xingang
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.2c06149