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Issue 66, 2019
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Recent advances in alkoxy radical-promoted C–C and C–H bond functionalization starting from free alcohols

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Abstract

Direct functionalization of inert C(sp3)–C(sp3) and C(sp3)–H bonds represents one of the most valuable synthetic tactics, yet large obstacles remain in terms of reactivity and selectivity. Alkoxy radicals enable C–C bond scission via β-C elimination and C(sp3)–H bond cleavage through a hydrogen atom transfer (HAT) process, thus providing an efficient method to address these problems. In view of atom- and step-economy, the direct use of abundant alcohols as alkoxy radical precursors in radical transformations is of high synthetic value. This feature article summarizes our recent achievements in (a) C(sp3)–C(sp3) bond cleavage via ring-opening of cycloalkanols and (b) site-specific C(sp3)–H functionalization of unprotected aliphatic alcohols, along with the reconstruction of various new chemical bonds, e.g. C–halogen, C–C, C–N, C–S, and C–Se bonds.

Graphical abstract: Recent advances in alkoxy radical-promoted C–C and C–H bond functionalization starting from free alcohols

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Article information


Submitted
22 Jun 2019
Accepted
19 Jul 2019
First published
19 Jul 2019

Chem. Commun., 2019,55, 9747-9756
Article type
Feature Article

Recent advances in alkoxy radical-promoted C–C and C–H bond functionalization starting from free alcohols

X. Wu and C. Zhu, Chem. Commun., 2019, 55, 9747
DOI: 10.1039/C9CC04785A

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