Direct transfer of tri- and di-fluoroethanol units enabled by radical activation of organosilicon reagents

Xiang Chen, Xingxing Gong, Zhengyu Li, Gang Zhou, Zhihong Zhu, Weilu Zhang, Shanshan Liu and Xiao Shen ()
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Xiang Chen: Wuhan University
Xingxing Gong: Wuhan University
Zhengyu Li: Wuhan University
Gang Zhou: Wuhan University
Zhihong Zhu: Wuhan University
Weilu Zhang: Wuhan University
Shanshan Liu: Wuhan University
Xiao Shen: Wuhan University

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: Abstract Trifluoroethanol and difluoroethanol units are important motifs in bioactive molecules, but the methods to direct incorporate these units are limited. Herein, we report two organosilicon reagents for the transfer of trifluoroethanol and difluoroethanol units into molecules. Through intramolecular C-Si bond activation by alkoxyl radicals, these reagents were applied in allylation, alkylation and alkenylation reactions, enabling efficient synthesis of various tri(di)fluoromethyl group substituted alcohols. The broad applicability and general utility of the approach are highlighted by late-stage introduction of these fluoroalkyl groups to complex molecules, and the synthesis of antitumor agent Z and its difluoromethyl analog Z′.

Date: 2020
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DOI: 10.1038/s41467-020-16380-9

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