Aerobic oxygenation of benzylic ketones promoted by a gold nanocluster catalyst

Hidehiro Sakurai, Ikuyo Kamiya, Hiroaki Kitahara, Hironori Tsunoyama, Tatsuya Tsukudad

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Gold nanoclusters stabilized by poly(N-vinyl-2-pyrrolidone) (Au:PVP) promote the oxidation of benzylic ketones, including auto-oxidation-type bond-cleavage reactions and α-hydroxylation, under ambient conditions. The catalyst accelerates the formation of an α-peroxide intermediate, from which bond cleavage spontaneously proceeds in aqueous solvent to give the auto-oxidation products. In contrast, the a-hydroxylation product is obtained predominantly in DMSO solvent.

Original languageEnglish
Pages (from-to)245-248
Number of pages4
JournalSynlett
Issue number2
DOIs
Publication statusPublished - 2009 Jan 1

Keywords

  • Auto-oxidation
  • Gold nanocluster
  • α-hydroxylation

ASJC Scopus subject areas

  • Organic Chemistry

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    Sakurai, H., Kamiya, I., Kitahara, H., Tsunoyama, H., & Tsukudad, T. (2009). Aerobic oxygenation of benzylic ketones promoted by a gold nanocluster catalyst. Synlett, (2), 245-248. https://doi.org/10.1055/s-0028-1087674