Tetrafluoroisopropylation of alkenes and alkynes enabled by photocatalytic consecutive difluoromethylation with CF2HSO2Na

Yuwei Hong, Jiayan Qiu, Zhenzhen Wu, Sangxuan Xu, Hanliang Zheng () and Gangguo Zhu ()
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Yuwei Hong: Zhejiang Normal University
Jiayan Qiu: Zhejiang Normal University
Zhenzhen Wu: Zhejiang Normal University
Sangxuan Xu: Zhejiang Normal University
Hanliang Zheng: Zhejiang Normal University
Gangguo Zhu: Zhejiang Normal University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract Direct assembly of complex fluorinated motifs from simple fluorine sources is an attractive frontier of synthetic chemistry. Reported herein is an unconventional protocol for achieving tetrafluoroisopropylation by using commercially available CF2HSO2Na as a convenient source of the tetrafluoroisopropyl [(CF2H)2CH] group, which finds widespread applications in life science and material science. Visible-light-induced hydrotetrafluoroisopropylation of alkenes and carbotetrafluoroisopropylation of alkynes have been thus developed. Various structurally diverse α-tetrafluoroisopropyl carbonyls and cyclopentanones are selectively constructed under mild conditions. A photocatalytic triple difluoromethylation cascade, driven by consecutive reductive radical/polar crossover processes, leads to the direct assembly of a tetrafluoroisopropyl moiety from CF2HSO2Na. This C1-to-C3 fluoroalkylation protocol provides a practical strategy for the rapid construction of polyfluorinated compounds that are otherwise difficult to access, thus significantly enhancing the boundary of fluoroalkylation chemistry.

Date: 2024
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DOI: 10.1038/s41467-024-50081-x

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