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Olefin cross-metathesis/Suzuki–Miyaura reactions on vinylphenylboronic acid pinacol esters

Olefin cross-metathesis/Suzuki–Miyaura reactions on vinylphenylboronic acid pinacol esters
Olefin cross-metathesis/Suzuki–Miyaura reactions on vinylphenylboronic acid pinacol esters
A series of alkenyl phenylboronic acid pinacol esters has been synthesized via an olefin cross-metathesis reaction of vinylphenylboronic acid pinacol ester derivatives. After catalytic hydrogenation, the resulting boronates were coupled via a microwave-mediated Suzuki-Miyaura reaction to afford a library of biarylethyl aryl and biarylethyl cycloalkyl derivatives. A complementary reaction sequence involved an initial Suzuki-Miyaura coupling.
0040-4039
1211-1217
Baltus, Christine B.
9345057c-8fc2-447d-aaf4-ee613ad4d131
Chuckowree, Irina S.
4d6d97df-dc13-4198-ac78-c8d5d80f77bf
Press, Neil J.
ee2e10f8-f371-4bf6-9c23-e385d0e16406
Day, Iain J.
63855d2b-1a0e-485e-b84f-9c1a6bca9a0e
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4
Baltus, Christine B.
9345057c-8fc2-447d-aaf4-ee613ad4d131
Chuckowree, Irina S.
4d6d97df-dc13-4198-ac78-c8d5d80f77bf
Press, Neil J.
ee2e10f8-f371-4bf6-9c23-e385d0e16406
Day, Iain J.
63855d2b-1a0e-485e-b84f-9c1a6bca9a0e
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4

Baltus, Christine B., Chuckowree, Irina S., Press, Neil J., Day, Iain J., Coles, Simon J., Tizzard, Graham J. and Spencer, John (2013) Olefin cross-metathesis/Suzuki–Miyaura reactions on vinylphenylboronic acid pinacol esters. Tetrahedron Letters, 54 (10), 1211-1217. (doi:10.1016/j.tetlet.2012.12.081).

Record type: Article

Abstract

A series of alkenyl phenylboronic acid pinacol esters has been synthesized via an olefin cross-metathesis reaction of vinylphenylboronic acid pinacol ester derivatives. After catalytic hydrogenation, the resulting boronates were coupled via a microwave-mediated Suzuki-Miyaura reaction to afford a library of biarylethyl aryl and biarylethyl cycloalkyl derivatives. A complementary reaction sequence involved an initial Suzuki-Miyaura coupling.

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More information

Published date: 6 March 2013
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry, Faculty of Natural and Environmental Sciences

Identifiers

Local EPrints ID: 352368
URI: http://eprints.soton.ac.uk/id/eprint/352368
ISSN: 0040-4039
PURE UUID: f9d2a8e4-a8d7-4f8e-bc9a-8b0cec471ec1
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779

Catalogue record

Date deposited: 13 May 2013 10:45
Last modified: 18 Feb 2021 16:57

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Contributors

Author: Christine B. Baltus
Author: Irina S. Chuckowree
Author: Neil J. Press
Author: Iain J. Day
Author: Simon J. Coles ORCID iD
Author: John Spencer

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