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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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Publication details

The article was received on 10 Jan 2012, accepted on 17 Feb 2012 and first published on 08 Mar 2012


Article type: Letter
DOI: 10.1039/C2NJ40021A
Citation: New J. Chem., 2012,36, 1141-1144
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    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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