Aerobic oxygenation of benzylic ketones promoted by a gold nanocluster catalyst

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

doi:10.1055/s-0028-1087674

Aerobic oxygenation of benzylic ketones promoted by a gold nanocluster catalyst

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

研究成果: Article › 査読

35 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	245-248
ページ数	4
ジャーナル	Synlett
号	2
DOI	https://doi.org/10.1055/s-0028-1087674
出版ステータス	Published - 2009 1月
外部発表	はい

ASJC Scopus subject areas

有機化学

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10.1055/s-0028-1087674

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AU - Sakurai, Hidehiro

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AU - Kitahara, Hiroaki

AU - Tsunoyama, Hironori

AU - Tsukudad, Tatsuya

PY - 2009/1

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N2 - 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.

AB - 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.

KW - Auto-oxidation

KW - Gold nanocluster

KW - α-hydroxylation

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Aerobic oxygenation of benzylic ketones promoted by a gold nanocluster catalyst

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