Issue 14, 2016

Carbene insertion into a P–H bond: parent phosphinidene–carbene adducts from PH3 and bis(phosphinidene)mercury complexes

Abstract

PH3 reacts with the in situ generated N-heterocyclic carbene DippNHC* (DippNHC* = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene) to give the phosphanyl–imidazolidine [DippNHC*-H]-[PH2]. Upon treatment with an ortho-quinone, [DippNHC*-H]-[PH2] is dehydrogenated to give the parent phosphinidene–carbene adduct DippNHC*[double bond, length as m-dash]PH. Alternative routes to [DippNHC*-H]-[PH2] and DippNHC*[double bond, length as m-dash]PH employ NaPH2 and (TMS)3P7 (TMS = trimethylsilyl), respectively, as phosphorus sources. The adduct DippNHC*[double bond, length as m-dash]PH and the related adduct DippNHC[double bond, length as m-dash]PH (DippNHC = bis(2,6-diisopropylphenyl)imidazol-2-ylidene) possessing an unsaturated NHC backbone both react with HgCl2 to give the bis(carbene–phosphinidenyl) complexes [(DippNHC*[double bond, length as m-dash]P)2Hg] and [(DippNHC[double bond, length as m-dash]P)2Hg].

Graphical abstract: Carbene insertion into a P–H bond: parent phosphinidene–carbene adducts from PH3 and bis(phosphinidene)mercury complexes

Supplementary files

Article information

Article type
Paper
Submitted
09 Mai 2015
Accepted
10 Jun 2015
First published
30 Jun 2015

Dalton Trans., 2016,45, 5999-6003

Author version available

Carbene insertion into a P–H bond: parent phosphinidene–carbene adducts from PH3 and bis(phosphinidene)mercury complexes

M. Bispinghoff, A. M. Tondreau, H. Grützmacher, C. A. Faradji and P. G. Pringle, Dalton Trans., 2016, 45, 5999 DOI: 10.1039/C5DT01741F

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