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

[1] Palladium-Catalyzed Cross-Coupling of Arylboronic Acid and Benzonitriles Using DMSO as the Methylene Source [J].

Ai, Han-Jun ;

Qi, Xinxin ;

Peng, Jin-Bao ;

Ying, Jun ;

Wu, Xiao-Feng .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (10) :2045-2048

[2] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].

Bellina, Fabio ;

Rossi, Renzo .

CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146

[3] Electrochemically Induced Intermolecular Cross-Dehydrogenative C-O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids [J].

Bityukov, Oleg V. ;

Matveeva, Olesya K. ;

Vil, Vera A. ;

Kokorekin, Vladimir A. ;

Nikishin, Gennady I. ;

Terent'ev, Alexander O. .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (03) :1448-1460

[4] NH2OH-HCl-Mediated Umpolung α-Methylsulfonylation of α-Sulfonyl Ketones with Methylsulfoxides: Synthesis of α,β-Bis-sulfonyl Arylketones [J].

Chang, Meng-Yang ;

Chen, Han-Yu ;

Tsai, Yu-Lin .

ORGANIC LETTERS, 2019, 21 (06) :1832-1836

[5] Fe(OTf)3-mediated synthesis of sulfonyl dihydropyrans [J].

Chang, Meng-Yang ;

Chen, Yu-Hsin ;

Cheng, Yu-Chieh .

TETRAHEDRON, 2016, 72 (04) :518-524

[6] One-Pot Access to Sulfonylmethyl Arylpyrroles via the Domino Aerobic Wacker-Type Aminocyclization/1,4-Sulfonyl Migration [J].

Chang, Meng-Yang ;

Cheng, Yu-Chieh ;

Lu, Yi-Ju .

ORGANIC LETTERS, 2014, 16 (23) :6252-6255

[7] Oxidative cleavage of α-sulfonyl ketones to carboxylic acids with Ce(NH4)2(NO3)6 [J].

Chang, Meng-Yang ;

Tsai, Chung-Yu .

TETRAHEDRON LETTERS, 2014, 55 (40) :5548-5550

[8] Synthesis of Arylethyl (E)-Styrylsulfones and Arylsulfones by One-Pot DIBAL-H/NaH-Mediated Reaction of β-Ketosulfones [J].

Chang, Meng-Yang ;

Chen, Yi-Chia ;

Chan, Chieh-Kai .

SYNLETT, 2014, 25 (12) :1739-1744

[9] Organocatalytic Carbon-Sulfur Bond-Forming Reactions [J].

Chauhan, Pankaj ;

Mahajan, Suruchi ;

Enders, Dieter .

CHEMICAL REVIEWS, 2014, 114 (18) :8807-8864

[10] Cs2CO3-promoted cross-dehydrogenative coupling of thiophenols with active methylene compounds [J].

Chen, Qian ;

Wang, Xiaofeng ;

Wen, Chunxiao ;

Huang, Yulin ;

Yan, Xinxing ;

Zeng, Jiekun .

RSC ADVANCES, 2017, 7 (63) :39758-39761

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