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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

35 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 language	English
Pages (from-to)	245-248
Number of pages	4
Journal	Synlett
Issue number	2
DOIs	https://doi.org/10.1055/s-0028-1087674
Publication status	Published - 2009 Jan 1

Keywords

Auto-oxidation
Gold nanocluster
α-hydroxylation

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-0028-1087674

Cite this

@article{5f9d9921078c4a7eb936968f6a54c943,

title = "Aerobic oxygenation of benzylic ketones promoted by a gold nanocluster catalyst",

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.",

keywords = "Auto-oxidation, Gold nanocluster, α-hydroxylation",

author = "Hidehiro Sakurai and Ikuyo Kamiya and Hiroaki Kitahara and Hironori Tsunoyama and Tatsuya Tsukudad",

year = "2009",

month = jan,

day = "1",

doi = "10.1055/s-0028-1087674",

language = "English",

pages = "245--248",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "2",

}

TY - JOUR

T1 - Aerobic oxygenation of benzylic ketones promoted by a gold nanocluster catalyst

AU - Sakurai, Hidehiro

AU - Kamiya, Ikuyo

AU - Kitahara, Hiroaki

AU - Tsunoyama, Hironori

AU - Tsukudad, Tatsuya

PY - 2009/1/1

Y1 - 2009/1/1

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

UR - http://www.scopus.com/inward/record.url?scp=62349127244&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=62349127244&partnerID=8YFLogxK

U2 - 10.1055/s-0028-1087674

DO - 10.1055/s-0028-1087674

M3 - Article

AN - SCOPUS:62349127244

SN - 0936-5214

SP - 245

EP - 248

JO - Synlett

JF - Synlett

IS - 2

ER -

Aerobic oxygenation of benzylic ketones promoted by a gold nanocluster catalyst

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this