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Enantioselective Copper-Catalyzed sp²/sp³ Diborylation of 1-Chloro-1-Trifluoromethylalkenes.

ABSTRACT: Fluorine-containing organoboron compounds have emerged as novel building blocks in chemical synthesis; among them, fluorinated sp²/sp³ diborylated compounds are particularly appealing, since they might undergo chemoselective and diversified transformations of different C-B bonds with fluorinated functionality, thus bringing versatility and complexity to the eventual products. However, expedient, synthetic strategies for the construction of such fluorinated diborylative compounds are very sparse. Herein, we disclose enantioselective Cu-catalyzed sp²/sp³ diborylations of 1-chloro-1-trifluoromethylalkenes, leading to diborylated compounds bearing a gem-difluoroalkenyl moiety; most intriguingly, the new formed C-B bonds include one stereoselective and optically pure Csp³-B bond. Further transformations on the eventual products demonstrated the values of our presented strategy.

SUBMITTER: Fan Z

PROVIDER: S-EPMC9413839 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Enantioselective Copper-Catalyzed sp2/sp3 Diborylation of 1-Chloro-1-Trifluoromethylalkenes.

Fan Zhenwei Z Ye Mingxing M Wang Yahao Y Qiu Jian J Li Wangyang W Ma Xingxing X Yang Kai K Song Qiuling Q

ACS central science 20220720 8

Fluorine-containing organoboron compounds have emerged as novel building blocks in chemical synthesis; among them, fluorinated sp2/sp3 diborylated compounds are particularly appealing, since they might undergo chemoselective and diversified transformations of different C-B bonds with fluorinated functionality, thus bringing versatility and complexity to the eventual products. However, expedient, synthetic strategies for the construction of such fluorinated diborylative comp ...[more]

PMID: 36032759

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