Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 45, Pages 19851-19856Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202007187
Keywords
alkoxyl radicals; cleavage reactions; DMSO; selectivity; silver
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Funding
- National Natural Science Foundation of China [21632001, 21772002, 81821004]
- Drug Innovation Major Project [2018ZX09711-001]
- Peking University [PKU2020PKYZX004]
- Open Research Fund of Shanghai Key Laboratory of Green Chemistry and Chemical Processes
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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.
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