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...

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Veröffentlicht in:ACS catalysis 2023-04, Vol.13 (7), p.4111-4119
Hauptverfasser: Rao, Na, Li, Yun-Ze, Luo, Yun-Cheng, Zhang, Yanxia, Zhang, Xingang
Format: Artikel
Sprache:eng
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Zusammenfassung: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