σ-Alkenyl endo-palladacycle formation via regiospecific functionalisation of an unreactive NHC-tethered C(sp2)–H bond

Michael R. Chapman; Christopher M. Pask; Alireza Ariafard; Charlotte E. Willans

doi:10.1039/C4CC10163D

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σ-Alkenyl endo-palladacycle formation via regiospecific functionalisation of an unreactive NHC-tethered C(sp²)–H bond†

Michael R. Chapman,^a Christopher M. Pask,^a Alireza Ariafard*^bc and Charlotte E. Willans*^a

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* Corresponding authors

^a School of Chemistry, University of Leeds, Woodhouse Lane, Leeds, UK

^b School of Chemistry, University of Tasmania, Private Bag 75, Hobart, Tasmania 7001, Australia

^c Department of Chemistry, Faculty of Science, Central Tehran Branch, Islamic Azad University, Shahrak Gharb, Tehran, Iran

Abstract

An unusual cyclometallation reaction at palladium is described, which proceeds via C–H functionalisation of a vinylic C(sp²)–H bond tethered to an NHC ligand. The energetic balance between palladacycle formation and bis-NHC complexation has been found to be very subtle.

This article is part of the themed collection: 2015 Emerging Investigators

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Article information

DOI: https://doi.org/10.1039/C4CC10163D
Article type: Communication
Submitted: 19 ⴷⵓⵊ 2014
Accepted: 22 ⵉⵏⵏ 2015
First published: 22 ⵉⵏⵏ 2015

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Chem. Commun., 2015,51, 5513-5515

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σ-Alkenyl endo-palladacycle formation via regiospecific functionalisation of an unreactive NHC-tethered C(sp²)–H bond

M. R. Chapman, C. M. Pask, A. Ariafard and C. E. Willans, Chem. Commun., 2015, 51, 5513 DOI: 10.1039/C4CC10163D

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