Effect of hydrogen bonding on ligand substitution and its implication for the Heck reaction



Ruan, Jiwu, Iggo, Jonathan A ORCID: 0000-0001-8070-1226 and Xiao, Jianliang ORCID: 0000-0003-2010-247X
(2019) Effect of hydrogen bonding on ligand substitution and its implication for the Heck reaction. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 880. pp. 150-155.

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Abstract

Simple hydrogen-bond donating ammonium cations are found to hydrogen-bond with the halo ligand of a key intermediate in the Heck reaction, [Pd(diphosphine)PhBr], and promote the substitution of the halide by a phosphine ligand. Furthermore, upon introduction of a hydorgne bond donor (HBD), the palladium intermediate reacts with an electron-rich olefin to afford the expected Heck product, whereas no reaction was observed without the HBD. These observations support the hypothesis that HBDs accelerate the Heck α-arylation via facilitating halide dissociation from palladium and thereby the ionic pathway.

Item Type: Article
Uncontrolled Keywords: Hydrogen bonding, Ligand substitution, Hydrogen bond donors, Heck reaction, Palladium catalysis
Depositing User: Symplectic Admin
Date Deposited: 13 Aug 2019 10:10
Last Modified: 19 Jan 2023 00:36
DOI: 10.1016/j.jorganchem.2018.11.010
Related URLs:
URI: https://livrepository.liverpool.ac.uk/id/eprint/3050922