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An evaluation of phosphine and carbene adducts of phosphite- and phosphinite-based palladacycles in the coupling of alkyl bromides with aryl boronic acids

An evaluation of phosphine and carbene adducts of phosphite- and phosphinite-based palladacycles in the coupling of alkyl bromides with aryl boronic acids
An evaluation of phosphine and carbene adducts of phosphite- and phosphinite-based palladacycles in the coupling of alkyl bromides with aryl boronic acids
A range of palladacyclic catalysts and their phosphine and carbene adducts were tested in the Suzuki coupling of an alkyl bromide with phenylboronic acid and showed modest activity in some cases. Unlike with aryl halide substrates it appears that there is no particular benefit in the use of palladacycles as the palladium source. Initial data indicate that the rate determining step is not the oxidative addition of the alkyl halide substrate, but rather lies later in the catalytic cycle.
alkyl halide, suzuki reaction, palladacycles, coupling, catalysis, high-activity catalysts, suzuki cross-couplings, bond-formingreactions, c-c, triarylphosphite complexes, beta-hydrogens, chlorides, halides, tosylates
0040-4020
9663-9669
Bedford, Robin B.
42532c45-cb80-48cd-9e93-8c2d5059eabe
Betham, Michael
0cd66656-1b0f-40b4-8dc7-a7b3121257f6
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Frost, Robert M.
fcce38bd-c584-443d-a6eb-bda4c97d5ee3
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Bedford, Robin B.
42532c45-cb80-48cd-9e93-8c2d5059eabe
Betham, Michael
0cd66656-1b0f-40b4-8dc7-a7b3121257f6
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Frost, Robert M.
fcce38bd-c584-443d-a6eb-bda4c97d5ee3
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28

Bedford, Robin B., Betham, Michael, Coles, Simon J., Frost, Robert M. and Hursthouse, Michael B. (2005) An evaluation of phosphine and carbene adducts of phosphite- and phosphinite-based palladacycles in the coupling of alkyl bromides with aryl boronic acids. Tetrahedron, 61 (41), 9663-9669. (doi:10.1016/j.tet.2005.07.097).

Record type: Article

Abstract

A range of palladacyclic catalysts and their phosphine and carbene adducts were tested in the Suzuki coupling of an alkyl bromide with phenylboronic acid and showed modest activity in some cases. Unlike with aryl halide substrates it appears that there is no particular benefit in the use of palladacycles as the palladium source. Initial data indicate that the rate determining step is not the oxidative addition of the alkyl halide substrate, but rather lies later in the catalytic cycle.

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More information

Published date: 10 October 2005
Keywords: alkyl halide, suzuki reaction, palladacycles, coupling, catalysis, high-activity catalysts, suzuki cross-couplings, bond-formingreactions, c-c, triarylphosphite complexes, beta-hydrogens, chlorides, halides, tosylates

Identifiers

Local EPrints ID: 20718
URI: https://eprints.soton.ac.uk/id/eprint/20718
ISSN: 0040-4020
PURE UUID: 3122a703-247d-4ac4-bc63-5afae06ffafe

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Date deposited: 01 Mar 2006
Last modified: 17 Jul 2017 16:28

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Contributors

Author: Robin B. Bedford
Author: Michael Betham
Author: Simon J. Coles
Author: Robert M. Frost
Author: Michael B. Hursthouse

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