Cu-catalyzed aerobic oxidative synthesis of sulfonamides from sulfonyl hydrazides and amines

被引:13
作者
Chung, Sohyun [1 ,2 ]
Kim, Jinho [1 ,2 ]
机构
[1] Incheon Natl Univ, Dept Chem, 119 Acad Ro, Incheon 22012, South Korea
[2] Incheon Natl Univ, Res Inst Basic Sci, 119 Acad Ro, Incheon 22012, South Korea
关键词
Aerobic oxidation; Copper catalysis; Sulfonyl hydrazides; Sulfonamides; Organic synthesis; OXYGENATION; ANTICANCER; ALCOHOLS; CLEAVAGE; ACCESS;
D O I
10.1016/j.tetlet.2019.02.016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An environmentally friendly route for sulfonamides has been developed. The oxidative coupling of sulfonyl hydrazides and amines was catalyzed by CuBr2 to produce various sulfonamides with the water and nitrogen gas as byproducts. Preliminary experiments revealed that the sulfonyl radical is likely to be involved in the reaction mechanism. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:792 / 795
页数:4
相关论文
共 47 条
[11]  
Haibo Z., 2015, CHEM COMMUN, V51, P16573
[12]   Expedient synthesis of sulfinamides from sulfonyl chlorides [J].
Harmata, Michael ;
Zheng, Pinguan ;
Huang, Chaofeng ;
Gomes, Maria G. ;
Ying, Weijiang ;
Ranyanil, Kanok-On ;
Balan, Gayatri ;
Calkins, Nathan L. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (02) :683-685
[13]   Copper-mediated S-N formation via an oxygen-activated radical process: a new synthesis method for sulfonamides [J].
Huang, Xin ;
Wang, Jichao ;
Ni, Zhangqin ;
Wang, Sichang ;
Pan, Yuanjiang .
CHEMICAL COMMUNICATIONS, 2014, 50 (35) :4582-4584
[14]  
Jones D.N., 1979, Comprehensive Organic Chemistry, V3
[15]   Oxidation Potential Tunable Organic Molecules and Their Catalytic Application to Aerobic Dehydrogenation of Tetrahydroquinolines [J].
Jung, Dahyeon ;
Jang, Seol Heui ;
Yim, Taeeun ;
Kim, Jinho .
ORGANIC LETTERS, 2018, 20 (20) :6436-6439
[16]   Cu-Catalyzed Aerobic Oxidation of Di-tert-butyl Hydrazodicarboxylate to Di-tert-butyl Azodicarboxylate and Its Application on Dehydrogenation of 1,2,3,4-Tetrahydroquinolines under Mild Conditions [J].
Jung, Dahyeon ;
Kim, Min Hye ;
Kim, Jinho .
ORGANIC LETTERS, 2016, 18 (24) :6300-6303
[17]   Robust Aerobic Alcohol Oxidation Catalyst Derived from Metal-Organic Frameworks [J].
Kim, Bo Ram ;
Oh, Jung Suk ;
Kim, Jinho ;
Lee, Chang Yeon .
CATALYSIS LETTERS, 2016, 146 (04) :734-743
[18]   Aerobic Oxidation of Alkyl 2-Phenylhydrazinecarboxylates Catalyzed by CuCl and DMAP [J].
Kim, Min Hye ;
Kim, Jinho .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (03) :1673-1679
[19]   I2/TBHP Mediated C-N and C-H Bond Cleavage of Tertiary Amines toward Selective Synthesis of Sulfonamides and β-Arylsulfonyl Enamines: The Solvent Effect on Reaction [J].
Lai, Junyi ;
Chang, Liming ;
Yuan, Gaoqing .
ORGANIC LETTERS, 2016, 18 (13) :3194-3197
[20]   A simple and eco-sustainable method for the sulfonylation of amines under microwave-assisted solvent-free conditions [J].
Lakrout, Salah ;
K'tir, Hacene ;
Amira, Aicha ;
Berredjem, Malika ;
Aouf, Nour-Eddine .
RSC ADVANCES, 2014, 4 (31) :16027-16032