Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer

Zhaoliang Yang, Yunhong Niu, Xiaoqian He, Suo Chen, Shanshan Liu, Zhengyu Li, Xiang Chen, Yunxiao Zhang, Yu Lan () and Xiao Shen ()
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Zhaoliang Yang: Wuhan University
Yunhong Niu: Wuhan University
Xiaoqian He: Chongqing University
Suo Chen: Wuhan University
Shanshan Liu: Wuhan University
Zhengyu Li: Wuhan University
Xiang Chen: Wuhan University
Yunxiao Zhang: Wuhan University
Yu Lan: Chongqing University
Xiao Shen: Wuhan University

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Controlling the reactivity of reactive intermediates is essential to achieve selective transformations. Due to the facile 1,5-hydrogen atom transfer (HAT), alkoxyl radicals have been proven to be important synthetic intermediates for the δ-functionalization of alcohols. Herein, we disclose a strategy to inhibit 1,5-HAT by introducing a silyl group into the α-position of alkoxyl radicals. The efficient radical 1,2-silyl transfer (SiT) allows us to make various α-functionalized products from alcohol substrates. Compared with the direct generation of α-carbon radicals from oxidation of α-C-H bond of alcohols, the 1,2-SiT strategy distinguishes itself by the generation of alkoxyl radicals, the tolerance of many functional groups, such as intramolecular hydroxyl groups and C-H bonds next to oxygen atoms, and the use of silyl alcohols as limiting reagents.

Date: 2021
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DOI: 10.1038/s41467-021-22382-y

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