Microwave-assisted Synthesis of Thioesters from Aldehydes and Thiols in Water

被引：13

作者：

Jhuang, Huei-Shu ^{[1
]}

Liu, Yi-Wei ^{[1
]}

Reddy, Daggula Mallikarjuna ^{[1
]}

Tzeng, Yong-Ze ^{[2
]}

Lin, Wei-Yu ^{[2
]}

Lee, Chin-Fa ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan

[2] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2018年 / 65卷 / 01期

关键词：

Aldehydes; Thiols; Microwave irradiation; Aqueous medium; Thioesters; CROSS-COUPLING REACTION; INTERMOLECULAR RADICAL REACTION; C-H FUNCTIONALIZATION; TRIFLUOROETHYL THIOESTERS; EFFICIENT SYNTHESIS; CATALYZED THIOESTERIFICATION; REDUCTIVE ACYLATION; ORGANIC DISULFIDES; NEUTRAL CONDITIONS; ACID-CHLORIDES;

D O I：

10.1002/jccs.201700045

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe the synthesis of thioesters via copper- or iron-catalyzed coupling of thiols with aldehydes on application of microwave irradiation. In this protocol, a variety of aliphatic and aromatic aldehydes and thiols were used, and the products were obtained in good to excellent yields.

引用

页码：24 / 27

页数：4

共 47 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] Towards organocatalytic polyketide synthases with diverse electrophile scope: Trifluoroethyl thioesters as nucleophiles in organocatalytic Michael reactions and beyond [J].

Alonso, Diego A. ;

Kitagaki, Shinji ;

Utsumi, Naoto ;

Barbas, Carlos F., III .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) :4588-4591

[3] Dess-Martin periodinane mediated synthesis of thioesters from aldehydes [J].

Bandgar, Sunita B. ;

Bandgar, B. P. ;

Korbad, B. L. ;

Sawant, S. S. .

TETRAHEDRON LETTERS, 2007, 48 (07) :1287-1290

[4]

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

[5] Synthesis of CuO on mesoporous silica and its applications for coupling reactions of thiols with aryl iodides [J].

Chen, Chin-Keng ;

Chen, Yan-Wun ;

Lin, Che-Hung ;

Lin, Hong-Ping ;

Lee, Chin-Fa .

CHEMICAL COMMUNICATIONS, 2010, 46 (02) :282-284

[6] Synthesis of Aryl Thioethers through the N-Chlorosuccinimide-Promoted Cross-Coupling Reaction of Thiols with Grignard Reagents [J].

Cheng, Jun-Hao ;

Ramesh, Chintakunta ;

Kao, Hsin-Lun ;

Wang, Yu-Jen ;

Chan, Chien-Ching ;

Lee, Chin-Fa .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) :10369-10374

[7] Highly regioselective synthesis of aryl chalcogenides through C-H functionalization of arenes [J].

Cheng, Jun-Hao ;

Yi, Chih-Lun ;

Liu, Tsung-Jui ;

Lee, Chin-Fa .

CHEMICAL COMMUNICATIONS, 2012, 48 (67) :8440-8442

[8] Reaction of Thioacids with Isocyanates and Isothiocyanates: A Convenient Amide Ligation Process [J].

Crich, David ;

Sasaki, Kaname .

ORGANIC LETTERS, 2009, 11 (15) :3514-3517

[9] Epimerization-Free Block Synthesis of Peptides from Thioacids and Amines with the Sanger and Mukaiyama Reagents [J].

Crich, David ;

Sharma, Indrajeet .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (13) :2355-2358

[10] Microwaves in organic synthesis.: Thermal and non-thermal microwave effects [J].

de la Hoz, A ;

Díaz-Ortiz, A ;

Moreno, A .

CHEMICAL SOCIETY REVIEWS, 2005, 34 (02) :164-178

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