Site-Selective C-H Functionalization-Sulfination Sequence to Access Aryl Sulfonamides

被引：95

作者：

Alvarez, Eva Maria ^{[1
]}

Plutschack, Matthew B. ^{[1
]}

Berger, Florian ^{[1
]}

Ritter, Tobias ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 12期

关键词：

PALLADIUM-CATALYZED SYNTHESIS; SULFUR-DIOXIDE SURROGATE; ONE-POT; SULFONYL FLUORIDES; BORONIC ACIDS; DABSO; BORYLATION; RONGALITE; REAGENTS; HALIDES;

D O I：

10.1021/acs.orglett.0c00982

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl sulfinates are precursors to a diverse number of sulfonyl-derived arenes, which are common motifs in pharmaceuticals and agrochemicals. Here, we report a site-selective two-step C-H sulfination sequence via aryl sulfonium salts to access aryl sulfonamides. Combined with site-selective aromatic thianthrenation, an operationally simple one-pot palladium-catalyzed protocol introduces the sulfonyl group using sodium hydroxymethylsulfinate (Rongalite) as a source of SO22-. The hydroxymethyl sulfone intermediate generated from the catalytic process can be employed as a synthetic handle to deliver a variety of sulfonyl-containing compounds.

引用

页码：4593 / 4596

页数：4

共 33 条

[21] Rongalite: A Useful Green Reagent in Organic Synthesis [J].

Kotha, Sambasivarao ;

Khedkar, Priti .

CHEMICAL REVIEWS, 2012, 112 (03) :1650-1680

[22] Photoredox catalysis with aryl sulfonium salts enables site-selective late-stage fluorination [J].

Li, Jiakun ;

Chen, Junting ;

Sang, Ruocheng ;

Ham, Won-Seok ;

Plutschack, Matthew B. ;

Berger, Florian ;

Chabbra, Sonia ;

Schnegg, Alexander ;

Genicot, Christophe ;

Ritter, Tobias .

NATURE CHEMISTRY, 2020, 12 (01) :56-62

[23] Nickel(II)-Catalyzed Synthesis of Sulfinates from Aryl and Heteroaryl Boronic Acids and the Sulfur Dioxide Surrogate DABSO [J].

Lo, Pui Kin Tony ;

Chen, Yiding ;

Willis, Michael C. .

ACS CATALYSIS, 2019, 9 (12) :10668-10673

[24] Synthesis of Sulfones from Organozinc Reagents, DABSO, and Alkyl Halides [J].

Rocke, Benjamin N. ;

Bahnck, Kevin B. ;

Herr, Michael ;

Lavergne, Sophie ;

Mascitti, Vincent ;

Perreault, Christian ;

Polivkova, Jana ;

Shavnya, Andrei .

ORGANIC LETTERS, 2014, 16 (01) :154-157

[25] para-C-H Borylation of Benzene Derivatives by a Bulky Iridium Catalyst [J].

Saito, Yutaro ;

Segawa, Yasutomo ;

Itami, Kenichiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) :5193-5198

[26] Site-selective C-H Oxygenation via Aryl Sulfonium Salts [J].

Sang, Ruocheng ;

Korkis, Stamatis E. ;

Su, Wanqi ;

Ye, Fei ;

Engl, Pascal S. ;

Berger, Florian ;

Ritter, Tobias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (45) :16161-16166

[27] Reaction of Alkyl Halides with Rongalite: One-Pot and Telescoped Syntheses of Aliphatic Sulfonamides, Sulfonyl Fluorides, and Unsymmetrical Sulfones [J].

Shavnya, Andre ;

Coffey, Steven B. ;

Hesp, Kevin D. ;

Ross, Stuart C. ;

Tsai, Andy S. .

ORGANIC LETTERS, 2016, 18 (22) :5848-5851

[28] Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol [J].

Tang, Ren-Jin ;

Milcent, Thierry ;

Crousse, Benoit .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (02) :930-938

[29] New catalytic reactions using sulfur dioxide [J].

Willis, Michael C. .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2019, 194 (07) :654-657

[30] DABCO-Bis(sulfur dioxide), DABSO, as a Convenient Source of Sulfur Dioxide for Organic Synthesis: Utility in Sulfonamide and Sulfamide Preparation [J].

Woolven, Holly ;

Gonzalez-Rodriguez, Carlos ;

Marco, Isabel ;

Thompson, Amber L. ;

Willis, Michael C. .

ORGANIC LETTERS, 2011, 13 (18) :4876-4878

← 1 2 3 4 →