Oxalates as Activating Groups for Tertiary Alcohols in Photoredox-Catalyzed gem-Difluoroallylation To Construct All-Carbon Quaternary Centers.

Construction of challenging and important all-carbon quaternary centers has received growing attention. Herein, with oxalates as activating groups for tertiary alcohols, we report photoredox-catalyzed gem-difluoroallylation to construct all-carbon quaternary centers enabled by efficient tertiary radical addition to α-trifluoromethyl alkenes. This transformation shows good functional group tolerance for both α-trifluoromethyl alkenes and oxalates. Moreover, this strategy is also successfully applied to the synthesis of monofluoralkenes from the corresponding electron-rich gem-difluoroalkenes and cesium tertiary alkyl oxalates under modified conditions.

Citation

Qing Wang, Ling Yue, Yanyang Bao, Yanan Wang, Danni Kang, Yan Gao, Zheliang Yuan. Oxalates as Activating Groups for Tertiary Alcohols in Photoredox-Catalyzed gem-Difluoroallylation To Construct All-Carbon Quaternary Centers. The Journal of organic chemistry. 2022 Jun 17;87(12):8237-8247

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PMID: 35612278

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