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

[1]

Anderson KK, 1979, SULFONIC ACIDS THEIR, V3, P331

[2] CHLOROSULFONATION OF AROMATIC AND HETEROAROMATIC SYSTEMS [J].

BASSIN, JP ;

CREMLYN, RJ ;

SWINBOURNE, FJ .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 56 (1-4) :245-275

[3] Site-selective and versatile aromatic C-H functionalization by thianthrenation [J].

Berger, Florian ;

Plutschack, Matthew B. ;

Riegger, Julian ;

Yu, Wanwan ;

Speicher, Samira ;

Ho, Matthew ;

Frank, Nils ;

Ritter, Tobias .

NATURE, 2019, 567 (7747) :223-228

[4] Copper(I)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling [J].

Chen, Yiding ;

Willis, Michael C. .

CHEMICAL SCIENCE, 2017, 8 (04) :3249-3253

[5] One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides [J].

Davies, Alyn T. ;

Curto, John M. ;

Bagley, Scott W. ;

Willis, Michael C. .

CHEMICAL SCIENCE, 2017, 8 (02) :1233-1237

[6] Synthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids [J].

DeBergh, J. Robb ;

Niljianskul, Nootaree ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (29) :10638-10641

[7] Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation [J].

Deeming, Alex S. ;

Russell, Claire J. ;

Willis, Michael C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (02) :747-750

[8] Combining Organometallic Reagents, the Sulfur Dioxide Surrogate DABSO, and Amines: A One-Pot Preparation of Sulfonamides, Amenable to Array Synthesis [J].

Deeming, Alex S. ;

Russell, Claire J. ;

Willis, Michael C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (04) :1168-1171

[9] Rediscovering the Chemistry of Sulfur Dioxide: New Developments in Synthesis and Catalysis [J].

Deeming, Alex S. ;

Emmett, Edward J. ;

Richards-Taylor, Charlotte S. ;

Willis, Michael C. .

SYNTHESIS-STUTTGART, 2014, 46 (20) :2701-2710

[10] DABSO-Based, Three-Component, One-Pot Sulfone Synthesis [J].

Deeming, Alex S. ;

Russell, Claire J. ;

Hennessy, Alan J. ;

Willis, Michael C. .

ORGANIC LETTERS, 2014, 16 (01) :150-153

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