Issue 2, 2013

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
31 Jul 2012
Accepted
05 Nov 2012
First published
06 Nov 2012

Chem. Sci., 2013,4, 691-695

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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