Direct Synthesis of (E)-β-(Thiocyanato)vinyl Sulfones by 1,2-Difunctionalization of Alkynes with Sulfinic Acids and Potassium Thiocyanate

被引：2

作者：

Jin, Haoru ^{[1
]}

Shi, Wei ^{[1
]}

Zhou, Chao ^{[1
]}

Li, Hongji ^{[1
]}

Wang, Lei ^{[1
,2
,3
,4
]}

Miao, Tao ^{[1
]}

机构：

[1] Huaibei Normal Univ, Dept Chem, Key Lab Green & Precise Synthet Chem & Applicat, Minist Educ, Huaibei 235000, Anhui, Peoples R China

[2] Taizhou Univ, Adv Res Inst, Taizhou 318000, Zhejiang, Peoples R China

[3] Taizhou Univ, Dept Chem, Taizhou 318000, Zhejiang, Peoples R China

[4] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 03期

基金：

中国国家自然科学基金; 美国国家科学基金会;

关键词：

Difunctionalization of alkynes; Sulfinic acids; Potassium thiocyanate; VINYL SULFONES; ARYLSULFINIC ACIDS; N-ARYLACRYLAMIDES; TERMINAL ALKYNES; SULFONYLATION; CATALYST; AMINOSULFONYLATION; ARYLSULFONYLATION; CYCLIZATION; CONVENIENT;

D O I：

10.1002/adsc.202301229

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A direct thiocyanatosulfonation of alkynes with sulfinic acids and potassium thiocyanate was developed at room temperature. This method provided a efficient and practical pathway to selectively access (E)-beta-(thiocyanato)vinyl sulfones by two C-S bonds formation in one step under metal-free condition. The advantages of this method included simple reaction conditions, easily available starting materials, good functional group compatibility, high regio- and stereoselectivity and good to excellent yields of products.

引用

页码：426 / 430

页数：5

共 6 条

[1] Direct difunctionalization of alkynes with sulfinic acids and molecular iodine: a simple and convenient approach to (E)-β-iodovinyl sulfones
Wei, Wei
Wen, Jiangwei
Yang, Daoshan
Jing, Huijun
You, Jinmao
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RSC ADVANCES, 2015, 5 (06): : 4416 - 4419
[2] Decarboxylative sulfonylation of arylpropiolic acids with sulfinic acids: synthesis of (E)-vinyl sulfones
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Katrun, Praewpan
Reutrakul, Vichai
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[3] Metal-Free Tunable 1,2-Difunctionalization of Terminal Alkynes: Synthesis of β-Substituted α,β-Unsaturated Ketones
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Ganie, Majid Ahmad
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CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (67)
[4] A Stereoselective Synthesis of (E)-Imidazo[1,2-a]-Pyridine gem-Keto Vinyl Sulfides, Vinyl Sulfoxides and Vinyl Sulfones
Sulfur Letters, 20 (06):
[5] Palladium-Catalyzed Conjugate Addition to Electron-Deficient Alkynes with Benzenesulfinic Acid Derived from 1,2-Bis(phenylsulfonyl)ethane: Selective Synthesis of (E)-Vinyl Sulfones
Song, Ren-Jie
Liu, Yu
Liu, Yan-Yun
Li, Jin-Heng
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (03): : 1001 - 1004
[6] Highly regio- and stereoselective palladium(0)-catalyzed addition of organoboronic acids with 1,2-allenic sulfones, sulfoxides, or alkyl- or aryl-substituted allenes in the presence of acetic acid:: An efficient synthesis of E-alkenes
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SYNTHESIS-STUTTGART, 2007, (17): : 2731 - 2745

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