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

26 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
Externally publishedYes

Fingerprint

Oxygenation
Nanoclusters
Ketones
Gold
Hydroxylation
Oxidation
Catalysts
Peroxides
Dimethyl Sulfoxide

Keywords

  • α-hydroxylation
  • Auto-oxidation
  • Gold nanocluster

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Aerobic oxygenation of benzylic ketones promoted by a gold nanocluster catalyst. / Sakurai, Hidehiro; Kamiya, Ikuyo; Kitahara, Hiroaki; Tsunoyama, Hironori; Tsukudad, Tatsuya.

In: Synlett, No. 2, 01.2009, p. 245-248.

Research output: Contribution to journalArticle

Sakurai, Hidehiro ; Kamiya, Ikuyo ; Kitahara, Hiroaki ; Tsunoyama, Hironori ; Tsukudad, Tatsuya. / Aerobic oxygenation of benzylic ketones promoted by a gold nanocluster catalyst. In: Synlett. 2009 ; No. 2. pp. 245-248.
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