Thioesterification of Alkylbenzenes with Thiols via Copper-Catalyzed Cross-Dehydrogenative Coupling without a Directing Group

被引:60
作者
Ali, Wajid [1 ]
Guin, Srimanta [1 ]
Rout, Saroj Kumar [1 ]
Gogoi, Anupal [1 ]
Patel, Bhisma K. [1 ]
机构
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, Assam, India
关键词
C-H activation; copper catalysis; cross-dehyrogenative coupling; thioesters; N BOND FORMATION; METAL-FREE; EFFICIENT SYNTHESIS; C-O; OXIDATIVE ESTERIFICATION; SULFONYL HYDRAZIDES; ONE-POT; AMINATION; ALDEHYDES; SULFENYLATION;
D O I
10.1002/adsc.201400360
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A unique copper-catalyzed cross-dehydrogenative coupling (CDC) of thiols and alkylbenzenes has been developed for the synthesis of thioesters without the assistance of any directing group. A thioester moiety is created via successive C-S and C-O bond formation at the expense of three sp(3) C-H bonds of the alkylbenzene and one sp(3) S-H bond of the thiol.
引用
收藏
页码:3099 / 3105
页数:7
相关论文
共 73 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]  
[Anonymous], 2012, ANGEW CHE
[3]  
[Anonymous], 2014, Angew. Chem
[4]  
[Anonymous], 2013, Angew. Chem.
[5]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[6]   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
[7]   Copper-Catalyzed Domino Oxidation-Acyloxylation Reaction of 2-Arylpyridines with Aldehydes or Methylarenes [J].
Bian, Yong-Jun ;
Xiang, Chang-Bing ;
Chen, Zhi-Ming ;
Huang, Zhi-Zhen .
SYNLETT, 2011, (16) :2407-2409
[8]   Palladium-catalyzed thiocarbonylation of iodoarenes with thiols in phosphonium salt ionic liquids [J].
Cao, Hong ;
McNamee, Laura ;
Alper, Howard .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3530-3534
[9]   Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction [J].
Chen, Long ;
Shi, Erbo ;
Liu, Zhaojun ;
Chen, Shulin ;
Wei, Wei ;
Li, Hong ;
Xu, Kai ;
Wan, Xiaobing .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) :4085-4089
[10]   Visible light-induced 3-sulfenylation of N-methylindoles with arylsulfonyl chlorides [J].
Chen, Min ;
Huang, Zhi-Tang ;
Zheng, Qi-Yu .
CHEMICAL COMMUNICATIONS, 2012, 48 (95) :11686-11688