Copper-Catalyzed Hydrosulfonylation of Alkynes Employing Sulfonohydrazides toward the Synthesis of Vinyl Sulfones

被引:14
作者
Hu, Deqing [1 ]
Bai, Feicheng [1 ]
Liu, Yunyun [1 ]
Wan, Jie-Ping [1 ]
机构
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
alkyne; sulfonohydrazide; hydrosulfonylation; copper catalysis; E-selectivity; CYSTEINE PROTEASE INHIBITORS; IODINE-MEDIATED SYNTHESIS; EFFICIENT ONE-POT; (E)-VINYL SULFONES; CINNAMIC-ACIDS; DECARBOXYLATIVE SULFONYLATION; METAL-FREE; SULFOXIDES; ALKENYLATION; OXIDATION;
D O I
10.1002/cjoc.201600337
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The hydrosulfonylation of terminal alkynes employing sulfonohydrazides has been accomplished with copper- catalysis in the presence of BPO (benzoic peroxyanhydride). Generally, excellent yield of the vinyl sulfone products has been acquired by heating the reaction at 70 degrees C in DMSO.
引用
收藏
页码:1053 / 1057
页数:5
相关论文
共 48 条
[1]   Stereoselective Synthesis of Z-α,β-Unsaturated Sulfones Using Peterson Reagents [J].
Ando, Kaori ;
Wada, Tomohiro ;
Okumura, Miho ;
Sumida, Hiroshi .
ORGANIC LETTERS, 2015, 17 (24) :6026-6029
[2]   Stereoselective Heck Reactions with Vinyl Sulfoxides, Sulfides and Sulfones [J].
Bachmann, Daniel G. ;
Wittwer, Christopher C. ;
Gillingham, Dennis G. .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) :3703-3707
[3]   Synthesis of sulfoxides by the hydrogen peroxide induced oxidation of sulfides catalyzed by iron tetrakis(pentafluorophenyl)porphyrin: Scope and chemoselectivity [J].
Baciocchi, E ;
Gerini, MF ;
Lapi, A .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3586-3589
[4]   Copper catalysis in organic synthesis [J].
Chemler, Sherry R. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 :2252-2253
[5]   Iodine-promoted decarboxylative C-S cross-coupling of cinnamic acids with sodium benzene sulfinates [J].
Chen, Jie ;
Mao, Jincheng ;
Zheng, Yang ;
Liu, Defu ;
Rong, Guangwei ;
Yan, Hong ;
Zhang, Cheng ;
Shi, Daqing .
TETRAHEDRON, 2015, 71 (31) :5059-5063
[6]   An Efficient Synthesis of Vinyl Sulfones from Alkenes and Aryl Sulfinates [J].
Das, Biswanath ;
Lingaiah, Maram ;
Damodar, Kongara ;
Bhunia, Nisith .
SYNTHESIS-STUTTGART, 2011, (18) :2941-2944
[7]   The first nucleophilic substitution reaction of organoindium reagents with sulfonyl chlorides: a facile method for preparation of vinyl sulfones [J].
Deng, Guisheng ;
Zou, Jingyuan .
ARKIVOC, 2010, :186-194
[8]   Vinyl Sulfone-Based Peptidomimetics as Anti-Trypanosomal Agents: Design, Synthesis, Biological and Computational Evaluation [J].
Dunny, Elizabeth ;
Doherty, William ;
Evans, Paul ;
Malthouse, J. Paul G. ;
Nolan, Derek ;
Knox, Andrew J. S. .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (17) :6638-6650
[9]   An efficient one-pot, three-component synthesis of vinyl sulfones via iodide-catalyzed radical alkenylation [J].
Fan, Weizheng ;
Su, Jiapeng ;
Shi, Dongyang ;
Feng, Bainian .
TETRAHEDRON, 2015, 71 (38) :6740-6743
[10]   Iodine-mediated synthesis of (E)-vinyl sulfones from sodium sulfinates and cinnamic acids in aqueous medium [J].
Gao, Jian ;
Lai, Junyi ;
Yuan, Gaoqing .
RSC ADVANCES, 2015, 5 (82) :66723-66726