Ultrasound-enhanced Ag-catalyzed decarboxylative coupling between α-keto acids and disulfides for the synthesis of thioesters

被引：21

作者：

Abenante, Laura ^{[1
]}

Penteado, Filipe ^{[1
]}

Vieira, Marcelo M. ^{[1
]}

Perin, Gelson ^{[1
]}

Alves, Diego ^{[1
]}

Lenardao, Eder J. ^{[1
]}

机构：

[1] Univ Fed Pelotas UFPel, CCQFA, Lab Sintese Organ Limpa LASOL, POB 354, BR-96010900 Pelotas, RS, Brazil

来源：

ULTRASONICS SONOCHEMISTRY | 2018年 / 49卷

关键词：

Sonochemistry; Thioester; Glyoxylic acids; Green chemistry; OXOCARBOXYLIC ACIDS; THIOL ESTERS; PHOTOREDOX CATALYSIS; BOND FORMATION; DIPHENYL DISELENIDE; MILD CONDITIONS; AQUEOUS-MEDIA; C-S; ACYLATION; EFFICIENT;

D O I：

10.1016/j.ultsonch.2018.07.014

中图分类号：

O42 [声学];

学科分类号：

070206 ; 082403 ;

摘要：

Herein, we described the ultrasound-assisted synthesis of thioesters via the Ag-catalyzed radical oxidative decarboxylation of alpha-keto acids, in the presence of disulfides. This protocol takes advantage of the sonication to prepare the title compounds in moderate to very good yields, in only 20 min of reaction. The positive effect of ultrasonic irradiation is attributed to both, the high mass transfer efficiency and to the induced radical formation in the reaction medium.

引用

页码：41 / 46

页数：6

共 69 条

[1] COBALT(II) CHLORIDE CATALYZED COUPLING OF THIOLS AND ANHYDRIDES - A NEW AND EFFICIENT SYNTHESIS OF THIOL ESTERS [J].

AHMAD, S ;

IQBAL, J .

TETRAHEDRON LETTERS, 1986, 27 (32) :3791-3794

[2] Rhodium-catalyzed reductive coupling of disulfides and diselenides with alkyl halides, using hydrogen as a reducing agent [J].

Ajiki, K ;

Hirano, M ;

Tanaka, K .

ORGANIC LETTERS, 2005, 7 (19) :4193-4195

[3]

[Anonymous], 1987, BIOCHEM SOC SYMP

[4]

Barbero M, 2003, SYNTHESIS-STUTTGART, P1225

[5] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636

[6]

Benaglia M, 2000, EUR J ORG CHEM, V2000, P563

[7]

Berzelius J. J, 1835, ANN PHYS, V36, P1

[8]

Cella R, 2012, HANDBOOK ON APPLICATIONS OF ULTRASOUND: SONOCHEMISTRY FOR SUSTAINABILITY, P263

[9] Silver-catalyzed decarboxylative acylation of arylglyoxylic acids with arylboronic acids [J].

Cheng, Kai ;

Zhao, Baoli ;

Qi, Chenze .

RSC ADVANCES, 2014, 4 (89) :48698-48702

[10] SYNTHESIS AND PROPERTIES OF THE ALPHA-KETO ACIDS [J].

COOPER, AJ ;

GINOS, JZ ;

MEISTER, A .

CHEMICAL REVIEWS, 1983, 83 (03) :321-358

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