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Aerobic oxygenation of phenylboronic acid promoted by thiol derivatives under gold-free conditions: a warning against gold nanoparticle catalysis |
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| Authors: | Patcharin Kaewmati Ekasith Somsook Raghu Nath DhitalHidehiro Sakurai |
| Institution: | a NANOCAST Laboratory, Center for Catalysis, Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Mahidol University, 272 Thung Phaya Thai, Rama VI Rd., Ratchathewi, Bangkok 10400, Thailand b Department of Functional Molecular Science, School of Physical Sciences, The Graduate University of Advanced Studies (SOKENDAI), Myodaiji, Okazaki 444-8787, Japan c Research Center for Molecular Scale Nanoscience, Institute for Molecular Science, Myodaiji, Okazaki 444-8787, Japan |
| 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. |
| Keywords: | Aerobic oxygenation Gold nanoparticle catalysis Phenol |
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