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Issue 2, 2013
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A metal–amide dependent, catalytic C–H functionalisation of triphenylphosphonium methylide

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Abstract

We report the [Y{N(SiMe3)2}3] catalysed dehydrocoupling of triphenylphosphonium methylide with phenylsilane to form the silylated ylide Ph3PCHSiH2Ph. Attempts to catalyse this reaction with the related group 2 hexamethyldisilazide base [Ca{N(SiMe3)2}2] led to the catalytic formation of the phosphine Ph2PCHSiH2Ph along with Ph2PMe in low selectivity, while group 1 bases [M{N(SiMe3)2}] (M = Li, Na, K) proved ineffective for both transformations. The stoichiometric reactions of Ph3PCH2 with [M{N(SiMe3)2}n] have been investigated and allowed the isolation and characterisation of a cyclometallated phosphonium methylide complex of yttrium.

Graphical abstract: A metal–amide dependent, catalytic C–H functionalisation of triphenylphosphonium methylide

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Publication details

The article was received on 31 Jul 2012, accepted on 05 Nov 2012 and first published on 06 Nov 2012


Article type: Edge Article
DOI: 10.1039/C2SC21123H
Citation: Chem. Sci., 2013,4, 691-695
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    A metal–amide dependent, catalytic C–H functionalisation of triphenylphosphonium methylide

    A. E. Nako, A. J. P. White and M. R. Crimmin, Chem. Sci., 2013, 4, 691
    DOI: 10.1039/C2SC21123H

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