Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF3•OEt2: An Approach to Symmetrical/Unsymmetrical Thiosulfonates

被引：91

作者：

Cao, Liang ^{[1
]}

Luo, Shi-He ^{[1
,3
]}

Jiang, Kai ^{[1
]}

Hao, Zhi-Feng ^{[2
]}

Wang, Bo-Wen ^{[1
]}

Pang, Chu-Ming ^{[1
]}

Wang, Zhao-Yang ^{[1
,3
]}

机构：

[1] South China Normal Univ, Sch Chem & Environm, Key Lab Theoret Chem Environm, Minist Educ, Guangzhou 510006, Guangdong, Peoples R China

[2] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Guangdong, Peoples R China

[3] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, 381 Wushan Rd, Guangzhou 510640, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 16期

关键词：

SULFONYL HYDRAZIDES; DIMETHYL-SULFOXIDE; DUAL CATALYSIS; BOND FORMATION; C-S; ACCESS; ARYL; REARRANGEMENT; ARYLATION; RADICALS;

D O I：

10.1021/acs.orglett.8b01808

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The BF3 center dot OEt2-mediated disproportionate coupling reaction of sodium sulfinates was found for the first time. In this reaction, various S-S(O)(2) bonds can be formed, efficiently giving thiosulfonates in moderate to excellent yields. As a convenient protocol for the synthesis of symmetrical and unsymmetrical thiosulfonates, its reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via a sulfinyl radical disproportionation. What is more, this transformation can also be applied practically as a gram-scale reaction and to the two-step synthesis of sulfone and sulfonamide in one pot in situ using thiosulfonate as an intermediate.

引用

页码：4754 / 4758

页数：5

共 66 条

[1] An evaluation of credentials of a multicomponent reaction for the synthesis of isothioureas through the use of a holistic CHEM21 green metrics toolkit [J].

Abou-Shehada, S. ;

Mampuys, P. ;

Maes, B. U. W. ;

Clark, J. H. ;

Summerton, L. .

GREEN CHEMISTRY, 2017, 19 (01) :249-258

[2] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636

[3] CHEMISTRY OF ALKYL THIOLSULFINATE ESTERS .6. PREPARATION AND SPECTRAL STUDIES [J].

BLOCK, E ;

OCONNOR, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (12) :3921-3929

[4] Metal-Free Sulfonylation of 3,4-Dihalo-2(5H)-furanones (X = Cl, Br) with Sodium Sulfinates under Air Atmosphere in Aqueous Media via a Radical Pathway [J].

Cao, Liang ;

Li, Jian-Xiao ;

Wu, Han-Qing ;

Jiang, Kai ;

Hao, Zhi-Feng ;

Luo, Shi-He ;

Wang, Zhao-Yang .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (03) :4147-4153

[5] Copper(I)-Catalyzed Alkyl- and Arylsulfenylation of 3,4-Dihalo-2(5H)-furanones (X= Br, Cl) with Sulfoxides under Mild Conditions [J].

Cao, Liang ;

Luo, Shi-He ;

Wu, Han-Qing ;

Chen, Liu-Qing ;

Jiang, Kai ;

Hao, Zhi-Feng ;

Wang, Zhao-Yang .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (17) :2961-2971

[6]

Caputo R., 1982, EUR CRYST M, V7, P165

[7] Metal-free disproportionation of formic acid mediated by organoboranes [J].

Chauvier, Clement ;

Thuery, Pierre ;

Cantat, Thibault .

CHEMICAL SCIENCE, 2016, 7 (09) :5680-5685

[8] Metal-free NaI/TBHP-mediated sulfonylation of thiols with sulfonyl hydrazides [J].

Chen, Qian ;

Huang, Yulin ;

Wang, Xiaofeng ;

Wu, Jiawei ;

Yu, Guodian .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (10) :1713-1719

[9] Acid-mediated sulfonylation of arylethynylene bromides with sodium arylsulfinates: synthesis of (E)-1,2-bis(arylsulfonyl)ethylenes and arylacetylenic sulfones [J].

Dai, Chenshu ;

Wang, Junqi ;

Deng, Siqi ;

Zhou, Candong ;

Zhang, Wenhe ;

Zhu, Qiuhua ;

Tang, Xiaodong .

RSC ADVANCES, 2017, 7 (57) :36112-36116

[10] Generation and decay of aryl sulfinyl and sulfenyl radicals: A transient absorption and computational study [J].

Darmanyan, AP ;

Gregory, DD ;

Guo, YS ;

Jenks, WS .

JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (37) :6855-6863

← 1 2 3 4 5 6 7 →