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Issue 5, 2012
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Oxidative functionalization of benzylic C–H bonds by DDQ

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Abstract

C–H activation of the methyl group of toluene and related ArCH3 derivatives by 2,3-dichloro-4,5-dicyano-1,4-benzoquinone (DDQ) gives insertion products, ArCH2O[C6Cl2(CN)2]OH via a rate-determining hydride abstraction by DDQ. The resulting benzylic ether can undergo reactions with phosphines to give benzylic phosphonium salts (Wittig reagents) and with phosphites to give phosphonate esters (Horner–Wadsworth–Emmons reagents).

Graphical abstract: Oxidative functionalization of benzylic C–H bonds by DDQ

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Supplementary files

Article information


Submitted
10 Jan 2012
Accepted
17 Feb 2012
First published
08 Mar 2012

New J. Chem., 2012,36, 1141-1144
Article type
Letter

Oxidative functionalization of benzylic C–H bonds by DDQ

V. S. Batista, R. H. Crabtree, S. J. Konezny, O. R. Luca and J. M. Praetorius, New J. Chem., 2012, 36, 1141
DOI: 10.1039/C2NJ40021A

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