Publication:
Aerobic oxygenation of phenylboronic acid promoted by thiol derivatives under gold-free conditions: A warning against gold nanoparticle catalysis

4

Issued Date

2012-11-07

Resource Type

Article

ISSN

18733581
00404039

DOI

10.1016/j.tetlet.2012.08.142

Other identifier(s)

2-s2.0-84867240441

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron Letters. Vol.53, No.45 (2012), 6104-6106

Suggested Citation

Patcharin Kaewmati, Ekasith Somsook, Raghu Nath Dhital, Hidehiro Sakurai Aerobic oxygenation of phenylboronic acid promoted by thiol derivatives under gold-free conditions: A warning against gold nanoparticle catalysis. Tetrahedron Letters. Vol.53, No.45 (2012), 6104-6106. doi:10.1016/j.tetlet.2012.08.142 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/13577

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Title

Aerobic oxygenation of phenylboronic acid promoted by thiol derivatives under gold-free conditions: A warning against gold nanoparticle catalysis

Author(s)

Patcharin Kaewmati
 Ekasith Somsook
 Raghu Nath Dhital
 Hidehiro Sakurai

Other Contributor(s)

Mahidol University
 Sokendai Graduate University for Advanced Studies
 National Institutes of Natural Sciences - Institute for Molecular Science

Abstract

Oxygenation of phenylboronic acid to phenol is promoted by thiol derivatives such as 2-aminothiophenol under aerobic conditions in water without metal catalyst. A plausible mechanism involves autoxidation of thiol to generate hydrogen peroxide in situ, which converts phenylboronic acid into phenol under basic conditions. Since thiols are often utilized as protective ligands for gold nanoparticles (AuNPs), this result is a warning that excess thiols and free thiols liberated from the Au surface could participate in aerobic oxidations catalyzed by thiol-protected AuNPs. © 2012 Elsevier Ltd. All rights reserved.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

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URI

https://repository.li.mahidol.ac.th/handle/123456789/13577

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Scopus 2011-2015