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.
Text
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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 |
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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 |