DMSO-Enabled Selective Radical O-H Activation of 1,3(4)-Diols
- 2 November 2020
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 59 (45), 19851-19856
- https://doi.org/10.1002/anie.202007187
Abstract
Control of selectivity is one of the central topics in organic chemistry. Although unprecedented alkoxyl-radical-induced transformations have drawn a lot of attention, compared to selective C-H activation, selective radical O-H activation remains less explored. Herein, we report a novel selective radical O-H activation strategy of diols by combining spatial effects with proton-coupled electron transfer (PCET). It was found that DMSO is an essential reagent that enables the regioselective transformation of diols. Mechanistic studies indicated the existence of the alkoxyl radical and the selective interaction between DMSO and hydroxyl groups. Moreover, the distal C-C cleavage was realized by this selective alkoxyl-radical-initiation protocol.Funding Information
- Collaborative Innovation Center of Major Machine Manufacturing in Liaoning (2018ZX09711-001)
- Peking University (PKU2020PKYZX004)
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