Empirical and computational insights into N-arylation reactions catalyzed by palladium meta-terarylphosphine catalyst

Empirical and computational insights into N-arylation reactions catalyzed by palladium meta-terarylphosphine catalyst
Title:
Empirical and computational insights into N-arylation reactions catalyzed by palladium meta-terarylphosphine catalyst
Other Titles:
ChemPlusChem
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Publication Date:
04 May 2017
Citation:
Yong, F. F.; Mak, A. M.; Wu, W. Q.; Sullivan, M. B.; Robins, E. G.; Johannes, C. W.; Jong, H.; Lim, Y. H., Empirical and computational insights into N-arylation reactions catalyzed by palladium meta-terarylphosphine catalyst. ChemPlusChem 2017, 82 (5), 750-757.
Abstract:
An in situ generated Pd–Cy*Phine catalyst has been successfully applied to the N‐arylation of primary and secondary amines, and it exhibited high performance across multiple substrate classes. The performance induced by the meta‐terarylphosphine motif of the Cy*Phine ligand for C−N cross‐coupling displayed only subtle differences to that of its biarylphosphine congener XPhos. DFT studies demonstrated comparable reaction energetics in the catalytic cycle steps for both Pd–Cy*Phine and Pd–XPhos, which was consistent with previous findings. The computational investigation also indicated that a putative rate‐determining step occurred after amine binding, which was likely to have annulled the expected benefits of having a meta‐terarylphosphine ligand architecture.
License type:
PublisherCopyrights
Funding Info:
A*STAR Joint Council Organisation 1st Developmental Programme Grant (Grant Number: JCO 1230400020)
Description:
This is the peer reviewed version of the following article: Yong, F. F.; Mak, A. M.; Wu, W. Q.; Sullivan, M. B.; Robins, E. G.; Johannes, C. W.; Jong, H.; Lim, Y. H., Empirical and computational insights into N-arylation reactions catalyzed by palladium meta-terarylphosphine catalyst. ChemPlusChem 2017, 82 (5), 750-757, which has been published in final form at https://doi.org/10.1002/cplu.201700042. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
ISSN:
2192-6506
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