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

被引：85

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 50 条

[31] Glycosylation of sialyl acetates with a novel catalyst combination:: Bismuth triflate and BF3•OEt2 system
Ikeda, K
Torisawa, Y
Nishi, T
Minamikawa, J
Tanaka, K
Sato, M
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (14) : 3073 - 3076
[32] Regioselective ring-opening of epoxides with ortho-lithioanisoles catalyzed by BF3•OEt2
Erturk, Erkan
Tezeren, Mustafa A.
Atalar, Taner
Tilki, Tahir
TETRAHEDRON, 2012, 68 (32) : 6463 - 6471
[33] A practical synthetic pathway to polysubstituted tetrahydropyridines via multicomponent reactions catalyzed by BF3•OEt2
Xiao, DJ
Wang, LJ
Feng, XM
SYNLETT, 2005, (10) : 1531 - 1534
[34] Chemoselective activation of aldimine in preference to aldehyde by the combination of BF3•OEt2 and water:: Novel catalyst for the Mannich-type reaction
Akiyama, T
Takaya, J
Kagoshima, H
CHEMISTRY LETTERS, 1999, (09) : 947 - 948
[35] Sulfide-BF3•OEt2 mediated Baylis-Hillman reactions
Walsh, LM
Winn, CL
Goodman, JM
TETRAHEDRON LETTERS, 2002, 43 (46) : 8219 - 8222
[36] Unique synthetic utility of BF3•OEt2 in the highly diastereoselective reduction of hydroxy carbonyl and dicarbonyl substrates
Ooi, T
Uraguchi, D
Morikawa, J
Maruoka, K
ORGANIC LETTERS, 2000, 2 (14) : 2015 - 2017
[37] An efficient selective reduction of aromatic azides to amines employing BF3•OEt2/NaI:: Synthesis of pyrrolobenzodiazepines
Kamal, Ahmed
Shankaraiah, N.
Markandeya, N.
Reddy, Ch. Sanjeeva
SYNLETT, 2008, (09) : 1297 - 1300
[38] Ethers as hydrogen sources in BF3•OEt2 promoted reduction of diphenylmethyl alcohols, ethers and esters to hydrocarbons
Li, Jiaqiang
Liu, Qing
Shen, Hang
Huang, Ruofeng
Zhang, Xiaohui
Xiong, Yan
Chen, Changguo
RSC ADVANCES, 2015, 5 (104): : 85291 - 85295
[39] An expeditious method to synthesize difluoroboron complexes of β-keto amides from β-keto nitriles and BF3•OEt2
Xu, Chuangchuang
Xu, Jiaxi
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (30) : 6375 - 6383
[40] XPS研究BF3·OEt2对HZSM—5沸石的脱铝作用
金亚明
南京师大学报(自然科学版), 1992, (03) : 52 - 56

← 1 2 3 4 5 →