Synthesis of 3-(Methylsulfonyl)benzo[b]thiophenes from Methyl(2-alkynylphenyl)sulfanes and Sodium Metabisulfite via a Radical Relay Strategy

被引：93

作者：

Gong, Xinxing ^{[1
,2
]}

Wang, Mengjiao ^{[2
]}

Ye, Shengqing ^{[1
]}

Wu, Jie ^{[1
,2
]}

机构：

[1] Taizhou Univ, Inst Adv Studies, 1139 Shifu Ave, Taizhou 318000, Peoples R China

[2] Fudan Univ, Dept Chem, 2005 Songhu Rd, Shanghai 200438, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 04期

基金：

中国国家自然科学基金;

关键词：

C-H METHYLATION; SULFUR-DIOXIDE; CATALYZED SYNTHESIS; 3-COMPONENT REACTION; ELECTROPHILIC CYCLIZATION; POTASSIUM METABISULFITE; MULTICOMPONENT REACTION; DIARYLIODONIUM SALTS; TERMINAL ALKYNES; S-METHYLATION;

D O I：

10.1021/acs.orglett.9b00100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A radical relay strategy for the generation of 3-(methylsulfonyl)benzo[b]thiophenes through a reaction of methyl(2-alkynylphenyl)sulfanes with sodium metabisulfite in the presence of a photocatalyst under visible light irradiation is developed. This photoinduced sulfonylation proceeds efficiently under mild conditions by using a catalytic amount of sodium methylsulfinate as an initiator. During the reaction process, the methyl radical generated in situ is the key intermediate, which undergoes a radical relay with the combination of sulfur dioxide to afford methylsulfonyl-containing compounds.

引用

页码：1156 / 1160

页数：5

共 102 条

[1] Adenylation and S-Methylation of Cysteine by the Bifunctional Enzyme TioN in Thiocoraline Biosynthesis [J].

Al-Mestarihi, Ahmad H. ;

Villamizar, German ;

Fernandez, Javier ;

Zolova, Olga E. ;

Lombo, Felipe ;

Garneau-Tsodikova, Sylvie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (49) :17350-17354

[2] Photopromoted Entry to Benzothiophenes, Benzoselenophenes, 3H-Indoles, Isocoumarins, Benzosultams, and (Thio)flavones by Gold-Catalyzed Arylative Heterocyclization of Alkynes [J].

Alcaide, Benito ;

Almendros, Pedro ;

Busto, Eduardo ;

Herrera, Fernando ;

Lazaro-Milla, Carlos ;

Luna, Amparo .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (15) :2640-2652

[3] The Methylation Effect in Medicinal Chemistry [J].

Barreiro, Eliezer J. ;

Kuemmerle, Arthur E. ;

Fraga, Carlos A. M. .

CHEMICAL REVIEWS, 2011, 111 (09) :5215-5246

[4] Taming sulfur dioxide: a breakthrough for its wide utilization in chemistry and biology [J].

Bisseret, Philippe ;

Blanchard, Nicolas .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (33) :5393-5398

[5] Heterocycle synthesis by copper facilitated addition of heteroatoms to alkenes, alkynes and arenes [J].

Chemler, Sherry R. ;

Fuller, Peter H. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1153-1160

[6] One-Pot, Three-Component Arylalkynyl Sulfone Synthesis [J].

Chen, C. Chun ;

Waser, Jerome .

ORGANIC LETTERS, 2015, 17 (03) :736-739

[7] Pd-Catalyzed, ortho C-H Methylation and Fluorination of Benzaldehydes Using Orthanilic Acids as Transient Directing Groups [J].

Chen, Xiao-Yang ;

Sorensen, Erik J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (08) :2789-2792

[8] Direct Copper-Catalyzed Three-Component Synthesis of Sulfonamides [J].

Chen, Yiding ;

Murray, Philip R. D. ;

Davies, Alyn T. ;

Willis, Michael C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (28) :8781-8787

[9] Parallel Synthesis of a Desketoraloxifene Analogue Library via lodocyclization/Palladium-Catalyzed Coupling [J].

Cho, Chul-Hee ;

Jung, Dai-Il ;

Neuenswander, Benjamin ;

Larock, Richard C. .

ACS COMBINATORIAL SCIENCE, 2011, 13 (05) :501-510

[10] Peroxide: A Novel Methylating Reagent [J].

Dai, Qiang ;

Jiang, Yan ;

Yu, Jin-Tao ;

Cheng, Jiang .

SYNTHESIS-STUTTGART, 2016, 48 (03) :329-339

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