Please use this identifier to cite or link to this item: https://doi.org/10.1016/S0022-328X(01)01074-9
Title: Palladium(II) ion promoted hydroamination of di(phenylethynyl)phenylphosphine and aniline: A facile synthesis of a six-membered P-N heterocycle
Authors: Liu, X.
Ong, T.K.W.
Selvaratnam, S. 
Vittal, J.J. 
White, A.J.P.
Williams, D.J.
Leung, P.-H. 
Keywords: Acid hydrolysis
Azaphospha heterocycle
Crystal structures
Hydroamination reaction
Imino-phosphine
Phosphinoalkyne
Issue Date: 1-Feb-2002
Source: Liu, X., Ong, T.K.W., Selvaratnam, S., Vittal, J.J., White, A.J.P., Williams, D.J., Leung, P.-H. (2002-02-01). Palladium(II) ion promoted hydroamination of di(phenylethynyl)phenylphosphine and aniline: A facile synthesis of a six-membered P-N heterocycle. Journal of Organometalic Chemistry 643-644 : 4-11. ScholarBank@NUS Repository. https://doi.org/10.1016/S0022-328X(01)01074-9
Abstract: The six-membered aromatic heterocycle 1,4-2H-1,2,4,6-tetraphenyl-1,4-azaphosphabenzene was generated efficiently via a [PdCl2(NCMe)2] promoted hydroamination between PhP(C=CPh)2 and aniline. The heterocyclization reaction adopts a stepwise mechanism during which the unstable intermediate imino complex cis-dichloro {1,2-diphenyl-3-phenyl(phenylethynyl)phosphino-1-aza-1-propene} palladium(II) is formed. The end product of the cyclization reaction is a palladium complex in which the six-membered aromatic P-N heterocyclic ring is coordinated to the metal center as a typical monodentate ligand via phosphorus. The azaphospha heterocycle can subsequently be liberated from the palladium reaction activator as an air-stable yellow solid by treating the palladium complex with KCN. In contrast to the intermediate imino-complex, where the C=N is readily hydrolyzed by HCl, the aromatic heterocycle is stable in strongly acidic environments. © 2002 Elsevier Science B.V. All rights reserved.
Source Title: Journal of Organometalic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/113203
ISSN: 0022328X
DOI: 10.1016/S0022-328X(01)01074-9
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