Rhodium-catalyzed synthesis of 2,3-diaryl-1,4-diketones via oxidative coupling of benzyl ketones using α-thioketone oxidizing reagent

Mieko Arisawa; Guangzhe Li; Masahiko Yamaguchi

doi:10.1016/j.tetlet.2012.12.107

Rhodium-catalyzed synthesis of 2,3-diaryl-1,4-diketones via oxidative coupling of benzyl ketones using α-thioketone oxidizing reagent

Mieko Arisawa, Guangzhe Li, Masahiko Yamaguchi

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

8 Citations (Scopus)

Abstract

RhH(PPh₃)₄ and 1,2-bis(diphenylphosphino)benzene (dppBz) catalyzed the oxidative coupling reaction of aryl benzyl ketones giving 2,3-diaryl-1,4-diketones in high yields. 3,3-Dimethyl-1-methylthio-2-butanone was used as the oxidizing reagent, which was converted to 3,3-dimethyl-2- butanone and dimethyl disulfide. Rhodium enolates were catalytically formed from ketones, which underwent oxidative coupling using an organosulfur reagent.

Original language	English
Pages (from-to)	1298-1301
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2012.12.107
Publication status	Published - 2013 Mar 6
Externally published	Yes

Keywords

2,3-Diaryl-1,4-diketone
Benzyl ketone
Oxidative coupling
Rhodium-catalyzed reaction
α-Thioketone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2012.12.107

Cite this

@article{dfb3fe1d25634832bdc4145e3657c6ca,

title = "Rhodium-catalyzed synthesis of 2,3-diaryl-1,4-diketones via oxidative coupling of benzyl ketones using α-thioketone oxidizing reagent",

abstract = "RhH(PPh3)4 and 1,2-bis(diphenylphosphino)benzene (dppBz) catalyzed the oxidative coupling reaction of aryl benzyl ketones giving 2,3-diaryl-1,4-diketones in high yields. 3,3-Dimethyl-1-methylthio-2-butanone was used as the oxidizing reagent, which was converted to 3,3-dimethyl-2- butanone and dimethyl disulfide. Rhodium enolates were catalytically formed from ketones, which underwent oxidative coupling using an organosulfur reagent.",

keywords = "2,3-Diaryl-1,4-diketone, Benzyl ketone, Oxidative coupling, Rhodium-catalyzed reaction, α-Thioketone",

author = "Mieko Arisawa and Guangzhe Li and Masahiko Yamaguchi",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (No. 21229001 ) and the GCOE program from JSPS. M.A. expresses her appreciation to the financial supports from the Grant-in-Aid for Scientific Research (No. 22689001 ), Japan Science Technology Agency, and also to the Asahi Glass Foundation. ",

year = "2013",

month = mar,

day = "6",

doi = "10.1016/j.tetlet.2012.12.107",

language = "English",

volume = "54",

pages = "1298--1301",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "10",

}

TY - JOUR

T1 - Rhodium-catalyzed synthesis of 2,3-diaryl-1,4-diketones via oxidative coupling of benzyl ketones using α-thioketone oxidizing reagent

AU - Arisawa, Mieko

AU - Li, Guangzhe

AU - Yamaguchi, Masahiko

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (No. 21229001 ) and the GCOE program from JSPS. M.A. expresses her appreciation to the financial supports from the Grant-in-Aid for Scientific Research (No. 22689001 ), Japan Science Technology Agency, and also to the Asahi Glass Foundation.

PY - 2013/3/6

Y1 - 2013/3/6

N2 - RhH(PPh3)4 and 1,2-bis(diphenylphosphino)benzene (dppBz) catalyzed the oxidative coupling reaction of aryl benzyl ketones giving 2,3-diaryl-1,4-diketones in high yields. 3,3-Dimethyl-1-methylthio-2-butanone was used as the oxidizing reagent, which was converted to 3,3-dimethyl-2- butanone and dimethyl disulfide. Rhodium enolates were catalytically formed from ketones, which underwent oxidative coupling using an organosulfur reagent.

AB - RhH(PPh3)4 and 1,2-bis(diphenylphosphino)benzene (dppBz) catalyzed the oxidative coupling reaction of aryl benzyl ketones giving 2,3-diaryl-1,4-diketones in high yields. 3,3-Dimethyl-1-methylthio-2-butanone was used as the oxidizing reagent, which was converted to 3,3-dimethyl-2- butanone and dimethyl disulfide. Rhodium enolates were catalytically formed from ketones, which underwent oxidative coupling using an organosulfur reagent.

KW - 2,3-Diaryl-1,4-diketone

KW - Benzyl ketone

KW - Oxidative coupling

KW - Rhodium-catalyzed reaction

KW - α-Thioketone

UR - http://www.scopus.com/inward/record.url?scp=84873122121&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84873122121&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2012.12.107

DO - 10.1016/j.tetlet.2012.12.107

M3 - Article

AN - SCOPUS:84873122121

VL - 54

SP - 1298

EP - 1301

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 10

ER -

Rhodium-catalyzed synthesis of 2,3-diaryl-1,4-diketones via oxidative coupling of benzyl ketones using α-thioketone oxidizing reagent

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this