Copper-Catalyzed Trifluoromethylthio-arylsulfonylation of Styrene Derivatives via the Insertion of Sulfur Dioxide

被引：29

作者：

Chen, Gang ^{[1
,2
]}

Xu, Jie ^{[1
,2
]}

Xiong, Baojian ^{[1
,2
]}

Song, Hongzhuo ^{[1
,2
]}

Zhang, Xuemei ^{[1
,2
]}

Ma, Xuelei ^{[3
,4
]}

Lian, Zhong ^{[1
,2
]}

机构：

[1] Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Dermatol, Chengdu 610041, Peoples R China

[2] Sichuan Univ, West China Hosp, Canc Ctr, Natl Clin Res Ctr Geriatr, Chengdu 610041, Peoples R China

[3] Sichuan Univ, West China Hosp, Dept Biotherapy, State Key Lab Biotherapy, Chengdu 610041, Peoples R China

[4] Sichuan Univ, West China Hosp, Canc Ctr, Chengdu 610041, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 05期

关键词：

TRANSFER RADICAL-ADDITION; AMINOSULFONYLATION; SULFONES; SO2;

D O I：

10.1021/acs.orglett.1c04371

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed four-component trifluoromethylthio-arylsulfonylation between styrene derivatives, AgSCF3, aryldiazonium tetrafluoroborates, and ex situ generated sulfur dioxide (from SOgen) is presented. This reaction features mild reaction conditions, good functional group tolerance, a broad substrate scope, good yields, and excellent diastereoselectivity. Preliminary mechanistic studies revealed that a radical process might be involved in this transformation.

引用

页码：1207 / 1212

页数：6

共 38 条

[1] Preparation of trifluoromethyl aryl sulfides using silver(I) trifluoromethanethiolate and an inorganic iodide [J].

Adams, DJ ;

Clark, JH .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1456-1460

[2] Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones [J].

Back, Thomas G. ;

Clary, Kristen N. ;

Gao, Detian .

CHEMICAL REVIEWS, 2010, 110 (08) :4498-4553

[3] Late stage trifluoromethylthiolation strategies for organic compounds [J].

Barata-Vallejo, Sebastian ;

Bonesi, Sergio ;

Postigo, Al .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (30) :7150-7182

[4] The role of organometallic copper(III) complexes in homogeneous catalysis [J].

Casitas, Alicia ;

Ribas, Xavi .

CHEMICAL SCIENCE, 2013, 4 (06) :2301-2318

[5] Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as a Nucleophilic CF3 Source [J].

Chu, Lingling ;

Qing, Feng-Ling .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1513-1522

[6] Enzymatic Carbon-Sulfur Bond Formation in Natural Product Biosynthesis [J].

Dunbar, Kyle L. ;

Scharf, Daniel H. ;

Litomska, Agnieszka ;

Hertweck, Christian .

CHEMICAL REVIEWS, 2017, 117 (08) :5521-5577

[7] The Development and Application of Sulfur Dioxide Surrogates in Synthetic Organic Chemistry [J].

Emmett, Edward J. ;

Willis, Michael C. .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (07) :602-611

[8] Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry [J].

Feng, Minghao ;

Tang, Bingqing ;

Liang, Steven H. ;

Jiang, Xuefeng .

CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (11) :1200-1216

[9] Radicals and Sulfur Dioxide: A Versatile Combination for the Construction of Sulfonyl-Containing Molecules [J].

Hofman, Kamil ;

Liu, Nai-Wei ;

Manolikakes, Georg .

CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (46) :11852-11863

[10] Visible-Light-Mediated Regioselective Chlorosulfonylation of Alkenes and Alkynes: Introducing the Cu(II) Complex [Cu(dap)Cl2] to Photochemical ATRA Reactions [J].

Hossain, Asik ;

Engl, Sebastian ;

Lutsker, Eugen ;

Reiser, Oliver .

ACS CATALYSIS, 2019, 9 (02) :1103-+

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