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RESEARCH ARTICLE
Contents Vol 69(5)

Investigation of Functional Group Effects on Palladium Catalysed Asymmetric P–H Addition*

Xi-Rui Li A , Renta Jonathan Chew A , Yongxin Li A and Pak-Hing Leung A B
+ Author Affiliations
- Author Affiliations

A Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.

B Corresponding author. Email: pakhing@ntu.edu.sg

Australian Journal of Chemistry 69(5) 499-504 https://doi.org/10.1071/CH15577
Submitted: 16 September 2015  Accepted: 15 October 2015   Published: 4 November 2015

Abstract

The pincer catalysed asymmetric P–H addition of diphenylphosphine to 3-benzylidene-2,4-pentadione is herein reported. Albeit successful in catalysing a series of similar substrates, unexpected chelation of the dione substrate to a CP and CN palladacycle catalyst resulted in inactivation of the catalyst with adjacent coordination sites. Protected phosphine adducts were isolated and characterised, providing critical insights to the choice of catalyst for structurally distinct functional groups borne by the substrate.


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[26]  CCDC 1424966 (Fig. 7) and 1424965 (Fig. 8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.