The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling

Robin Bedford; Peter B Brenner; David Elorriaga; Jeremy Harvey; Joshua Nunn

doi:10.1039/C6DT01823H

The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling

Robin Bedford, Peter B Brenner, David Elorriaga, Jeremy Harvey, Joshua Nunn

School of Chemistry

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Abstract

The application of a variety of iron complexes with chelating amine ligands as pre-catalysts in the representative cross-coupling of 4-tolylmagnesium bromide with cyclohexyl bromide was investigated. The results from this study indicate the the performance of the pre-catalyst is inversely proportional to the strength of the chelate or macrocyclic effect of the amine ligand, as determined by the propensity of the ligand to be displaced from the iron centre by reaction with excess benzyl magnesium chloride. The findings from this study are consistent with a catalytic cycle wherein the chelating amine ligand is not coordinated to the iron centre during turnover.

Original language	English
Pages (from-to)	15811-15817
Number of pages	7
Journal	Dalton Transactions
Volume	45
Issue number	40
Early online date	16 Jun 2016
DOIs	https://doi.org/10.1039/C6DT01823H
Publication status	Published - 28 Oct 2016

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The Ironworks: a mechanistic foundry for iron-catalysed cross-coupling
Bedford, R. B. (Principal Investigator)
1/03/13 → 31/07/17
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research

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title = "The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling",

abstract = "The application of a variety of iron complexes with chelating amine ligands as pre-catalysts in the representative cross-coupling of 4-tolylmagnesium bromide with cyclohexyl bromide was investigated. The results from this study indicate the the performance of the pre-catalyst is inversely proportional to the strength of the chelate or macrocyclic effect of the amine ligand, as determined by the propensity of the ligand to be displaced from the iron centre by reaction with excess benzyl magnesium chloride. The findings from this study are consistent with a catalytic cycle wherein the chelating amine ligand is not coordinated to the iron centre during turnover.",

author = "Robin Bedford and Brenner, {Peter B} and David Elorriaga and Jeremy Harvey and Joshua Nunn",

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T1 - The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling

AU - Bedford, Robin

AU - Brenner, Peter B

AU - Elorriaga, David

AU - Harvey, Jeremy

AU - Nunn, Joshua

PY - 2016/10/28

Y1 - 2016/10/28

N2 - The application of a variety of iron complexes with chelating amine ligands as pre-catalysts in the representative cross-coupling of 4-tolylmagnesium bromide with cyclohexyl bromide was investigated. The results from this study indicate the the performance of the pre-catalyst is inversely proportional to the strength of the chelate or macrocyclic effect of the amine ligand, as determined by the propensity of the ligand to be displaced from the iron centre by reaction with excess benzyl magnesium chloride. The findings from this study are consistent with a catalytic cycle wherein the chelating amine ligand is not coordinated to the iron centre during turnover.

AB - The application of a variety of iron complexes with chelating amine ligands as pre-catalysts in the representative cross-coupling of 4-tolylmagnesium bromide with cyclohexyl bromide was investigated. The results from this study indicate the the performance of the pre-catalyst is inversely proportional to the strength of the chelate or macrocyclic effect of the amine ligand, as determined by the propensity of the ligand to be displaced from the iron centre by reaction with excess benzyl magnesium chloride. The findings from this study are consistent with a catalytic cycle wherein the chelating amine ligand is not coordinated to the iron centre during turnover.

U2 - 10.1039/C6DT01823H

DO - 10.1039/C6DT01823H

M3 - Article (Academic Journal)

SN - 1477-9226

VL - 45

SP - 15811

EP - 15817

JO - Dalton Transactions

JF - Dalton Transactions

IS - 40

ER -

The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling

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The Ironworks: a mechanistic foundry for iron-catalysed cross-coupling

3-month Core Capability for Chemistry Research

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