Microwave-mediated synthesis of an arylboronate library
Microwave-mediated synthesis of an arylboronate library
A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1-3) respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.
suzuki coupling, microwave, boronic acid, nucleophilic substitution, biaryls, supported reagents
24-31
Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4
Baltus, Christine B.
9345057c-8fc2-447d-aaf4-ee613ad4d131
Patel, Hiren
73682df0-69ba-44c9-88b2-5c19f7f23677
Press, Neil J.
ee2e10f8-f371-4bf6-9c23-e385d0e16406
Callear, Samantha K.
5af7f651-0ff0-4163-80b3-34996d62022a
Male, Louise
89b88c4f-2308-4b94-8f3a-2dc537a66533
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
2011
Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4
Baltus, Christine B.
9345057c-8fc2-447d-aaf4-ee613ad4d131
Patel, Hiren
73682df0-69ba-44c9-88b2-5c19f7f23677
Press, Neil J.
ee2e10f8-f371-4bf6-9c23-e385d0e16406
Callear, Samantha K.
5af7f651-0ff0-4163-80b3-34996d62022a
Male, Louise
89b88c4f-2308-4b94-8f3a-2dc537a66533
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Spencer, John, Baltus, Christine B., Patel, Hiren, Press, Neil J., Callear, Samantha K., Male, Louise and Coles, Simon J.
(2011)
Microwave-mediated synthesis of an arylboronate library.
ACS Combinatorial Science, 13 (1), .
(doi:10.1021/co100011g).
Abstract
A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1-3) respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.
This record has no associated files available for download.
More information
e-pub ahead of print date: 10 November 2010
Published date: 2011
Keywords:
suzuki coupling, microwave, boronic acid, nucleophilic substitution, biaryls, supported reagents
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 346133
URI: http://eprints.soton.ac.uk/id/eprint/346133
ISSN: 2156-8952
PURE UUID: 500afeda-b9b3-428f-b443-e5dfc0264d8e
Catalogue record
Date deposited: 14 Jan 2013 13:52
Last modified: 15 Mar 2024 03:01
Export record
Altmetrics
Contributors
Author:
John Spencer
Author:
Christine B. Baltus
Author:
Hiren Patel
Author:
Neil J. Press
Author:
Samantha K. Callear
Author:
Louise Male
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics
