Iodine-catalyzed sulfonylation of sulfonyl hydrazides with tert-amines: a green and efficient protocol for the synthesis of sulfonamides

被引：13

作者：

Chen, Jinyang ^{[1
]}

Han, Xiaoran ^{[1
]}

Mei, Lan ^{[1
]}

Liu, Jinchuan ^{[1
]}

Du, Kui ^{[1
]}

Cao, Tuanwu ^{[1
]}

Li, Qiang ^{[2
]}

机构：

[1] Yangtze Normal Univ, Coll Chem & Chem Engn, Chongqing 408000, Peoples R China

[2] Liaocheng Univ, Sch Chem & Chem Engn, Inst Funct Organ Mol & Mat, 1 Hunan St, Liaocheng 252059, Shandong, Peoples R China

来源：

RSC ADVANCES | 2019年 / 9卷 / 54期

基金：

中国国家自然科学基金;

关键词：

QUINOLINE N-OXIDES; ONE-POT SYNTHESIS; C-N; STEREOSELECTIVE SULFONYLATION; BOND-CLEAVAGE; ARYL HALIDES; METAL; ARYLATION; CHLORIDES; REAGENTS;

D O I：

10.1039/c9ra07361b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This study provides a direct, sustainable and eco-friendly method for the synthesis of various sulfonamides via the sulfonylation of sulfonyl hydrazides with tert-amines. The method utilizes sulfonyl hydrazides to oxidize and couple with tertiary amines through selective cleavage of C-N bonds. In this reaction, molecular iodine was used as the catalyst and t-butyl hydroperoxide was used as the oxidant.

引用

页码：31212 / 31216

页数：5

共 66 条

[1] A General Copper Powder-Catalyzed Ullmann-Type Reaction of 3-Halo-4(1H)-quinolones With Various Nitrogen-Containing Nucleophiles [J].

Audisio, Davide ;

Messaoudi, Samir ;

Peyrat, Jean-Francois ;

Brion, Jean-Daniel ;

Alami, Mouad .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (12) :4995-5005

[2] Copper-Mediated N-Heteroarylation of Primary Sulfonamides: Synthesis of Mono-N-heteroaryl Sulfonamides [J].

Baffoe, Jonathan ;

Hoe, Madelene Y. ;

Toure, B. Barry .

ORGANIC LETTERS, 2010, 12 (07) :1532-1535

[3] Direct Conversion of Thiols to Sulfonyl Chlorides and Sulfonamides [J].

Bahrami, Kiumars ;

Khodaei, Mohammad M. ;

Soheilizadt, Mehdi .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) :9287-9291

[4] Direct synthesis of sulfonamides and activated sulfonate esters from sulfonic acids [J].

Caddick, S ;

Wilden, JD ;

Judd, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (04) :1024-1025

[5] The concept of dual roles design in clean organic preparation [J].

Cao, Zhong ;

Zhu, Qin ;

Lin, Ying-Wu ;

He, Wei-Min .

CHINESE CHEMICAL LETTERS, 2019, 30 (12) :2132-2138

[6] Neighbouring group assisted sulfonamide cleavage of sharpless aminols under acetonation conditions [J].

Chandrasekhar, S ;

Mohapatra, S .

TETRAHEDRON LETTERS, 1998, 39 (07) :695-698

[7] Visible light-mediated dehydrogenative β-arylsulfonylation of tertiary aliphatic amines with arylsulfonyl chlorides [J].

Chen, Min ;

Huang, Zhi-Tang ;

Zheng, Qi-Yu .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (46) :9337-9340

[8] Sulfonylation of C(sp3)-H bond for synthesis of 2-sulfolmethyl azaarenes catalyzed by TBAI in water [J].

Dong, Dao-Qing ;

Gao, Xing ;

Li, Li-Xia ;

Hao, Shuang-Hong ;

Wang, Zu-Li .

RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (12) :7557-7567

[9] Transformation of aldehydes or alcohols to amides at room temperature under aqueous conditions [J].

Dong, Dao-Qing ;

Hao, Shuang-Hong ;

Zhang, Hui ;

Wang, Zu-Li .

CHINESE CHEMICAL LETTERS, 2017, 28 (07) :1597-1599

[10] A general iodine-mediated synthesis of primary sulfonamides from thiols and aqueous ammonia [J].

Feng, Jian-Bo ;

Wu, Xiao-Feng .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (29) :6951-6954

← 1 2 3 4 5 6 7 →