Direct Sp3 α-C–H activation and functionalization of alcohol and ether

Shu-Yu Zhang; Fu-Min Zhang; Yong-Qiang Tu

doi:10.1039/C0CS00063A

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Direct Sp³ α-C–H activation and functionalization of alcohol and ether†

Shu-Yu Zhang,^a Fu-Min Zhang^a and Yong-Qiang Tu*^a

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* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China

Abstract

Seven kinds of sp³ α-C–H activation/C–C formation reactions of alcohols and ethers have been reviewed in this tutorial review, from the viewpoint of both methodology and synthetic application, towards the efficiency, chemo-, regio- and stereoselectivity, catalytic system, substrate scope and mechanistic study. Section 2 describes radical-mediated α-C–H activation and addition/elimination of ethers with unsaturated (C [double bond, length as m-dash] C and C [triple bond, length as m-dash] C) species. Sections 3–8 discuss the α-C–H activation and additions of alcohols and/or ethers with unsaturated (CC, CC, CO and CN) compounds, which involve the key processes of radical mediation, carbenoid insertion, 1,5-H-migration, oxidative dehydrogenation coupling, transfer hydrogenative coupling, and metal-mediated C [double bond, length as m-dash] C insertion into the C–H bond.

This article is part of the themed collection: C–H Functionalisation in organic synthesis

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Article information

DOI: https://doi.org/10.1039/C0CS00063A
Article type: Tutorial Review
Submitted: 03 Aug 2010
First published: 02 Feb 2011

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Chem. Soc. Rev., 2011,40, 1937-1949

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Direct Sp³ α-C–H activation and functionalization of alcohol and ether

S. Zhang, F. Zhang and Y. Tu, Chem. Soc. Rev., 2011, 40, 1937 DOI: 10.1039/C0CS00063A

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