Acid-Controlled Access to β-Sulfenyl Ketones and α,β-Disulfonyl Ketones by Pummerer Reaction of β-Keto Sulfones and Sulfoxides

被引：14

作者：

Fan, Jian ^{[1
]}

Zhao, Yiming ^{[1
]}

Zhang, Jitan ^{[1
]}

Xie, Meihua ^{[1
]}

Zhang, Yuzhong ^{[1
]}

机构：

[1] Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Mol Based Mat, Minist Educ,Key Lab Funct Mol Solids, Wuhu 241002, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 02期

基金：

中国国家自然科学基金;

关键词：

C-H BONDS; DIMETHYL-SULFOXIDE; METHYL KETONES; VINYL HALIDES; SULFUR; DMSO; FUNCTIONALIZATION; CASCADE; ARYL; SULFONYLATION;

D O I：

10.1021/acs.joc.9b02766

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient acid-mediated reaction of beta-keto sulfones with sulfoxides under metal-free conditions has been developed, thereby delivering the acid-controlled synthesis of beta-sulfenyl ketones and alpha,beta-disulfonyl ketones in good to excellent yields. The mechanism of the transformations has been studied carefully, which suggested the involvement of a radical process in the formation of alpha,beta-disulfonyl ketones.

引用

页码：691 / 701

页数：11

共 73 条

[21] Copper-Catalyzed Coupling Reactions of Cyclobutanone Oxime Esters with Sulfur Nucleophiles at Room Temperature [J].

He, Mingchuang ;

Yan, Zhaohua ;

Zhu, Fuyuan ;

Lin, Sen .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (24) :15438-15448

[22] An Unexpected Michael Aldol Smiles Rearrangement Sequence for the Synthesis of Versatile Optically Active Bicyclic Structures by Using Asymmetric Organocatalysis [J].

Holub, Nicole ;

Jiang, Hao ;

Paixao, Marcio W. ;

Tiberi, Caterina ;

Jorgensen, Karl A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (14) :4337-4346

[23] CuI mediated synthesis of sulfonyl dihydrofurans [J].

Hsueh, Nai-Chen ;

Hsiao, Yu-Ting ;

Chang, Meng-Yang .

TETRAHEDRON, 2017, 73 (30) :4398-4406

[24] Highly mono-selective ortho-methylthiolation of benzamides via cobalt-catalyzed sp2 C-H activation [J].

Hu, Liang ;

Chen, Xiang ;

Yu, Lin ;

Yu, Yongqi ;

Tan, Ze ;

Zhu, Gangguo ;

Gui, Qingwen .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (02) :216-221

[25] Visible-light-induced methylsulfonylation/bicyclization of C(sp3)-tethered 1,7-enynes using a DMSO/H2O system [J].

Huang, Min-Hua ;

Zhu, Chi-Fan ;

He, Chun-Lan ;

Zhu, Yi-Long ;

Hao, Wen-Juan ;

Wang, De-Cai ;

Tu, Shu-Jiang ;

Jiang, Bo .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (10) :1643-1650

[26] Scandium-catalyzed electrophilic alkene difunctionalization: regioselective synthesis of thiosulfone derivatives [J].

Huang, Shuai ;

Li, Haoyu ;

Xie, Tian ;

Wei, Fang ;

Tung, Chen-Ho ;

Xu, Zhenghu .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (10) :1663-1666

[27] Functionalization of Organic Molecules by Transition-Metal-Catalyzed C(sp3)-H Activation [J].

Jazzar, Rodolphe ;

Hitce, Julien ;

Renaudat, Alice ;

Sofack-Kreutzer, Julien ;

Baudoin, Olivier .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (09) :2654-2672

[28] Catalytic and direct methyl sulfonylation of alkenes and alkynes using a methyl sulfonyl radical generated from a DMSO, dioxygen and copper system [J].

Jiang, Yaojia ;

Loh, Teck-Peng .

CHEMICAL SCIENCE, 2014, 5 (12) :4939-4943

[29] Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts [J].

Kaiser, Daniel ;

Klose, Immo ;

Oost, Rik ;

Neuhaus, James ;

Maulide, Nuno .

CHEMICAL REVIEWS, 2019, 119 (14) :8701-8780

[30] Access to 2-naphthols via Ru(ii)-catalyzed C-H annulation of nitrones with α-diazo sulfonyl ketones [J].

Kong, Lingheng ;

Han, Xi ;

Li, Xingwei .

CHEMICAL COMMUNICATIONS, 2019, 55 (51) :7339-7342

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