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

被引：216

作者：

Deeming, Alex S. ^{[1
]}

Russell, Claire J. ^{[2
]}

Willis, Michael C. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Syngenta, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

electrophiles; oxidation; palladium; sulfur; synthetic methods; SULFUR-DIOXIDE SURROGATE; PALLADIUM-CATALYZED AMINOSULFONYLATION; SULFONE SYNTHESIS; ONE-POT; ARYL HALIDES; DIARYLIODONIUM SALTS; ARYLBORONIC ACIDS; ALKYL-HALIDES; 3-COMPONENT; SULFONAMIDES;

D O I：

10.1002/anie.201508370

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A redox-neutral palladium(II)-catalyzed conversion of aryl, heteroaryl, and alkenyl boronic acids into sulfinate intermediates, and onwards to sulfones and sulfonamides, has been realized. A simple Pd(OAc) 2 catalyst, in combination with the sulfur dioxide surrogate 1,4-diazabicyclo[ 2.2.2] octane bis(sulfur dioxide) (DABSO), is sufficient to achieve rapid and high-yielding conversion of the boronic acids into the corresponding sulfinates. Addition of C-or N-based electrophiles then allows conversion into sulfones and sulfonamides, respectively, in a one-pot, two-step process.

引用

页码：747 / 750

页数：4

共 51 条

[21] A Practical, One-Pot Synthesis of Sulfonylated Pyridines [J].

Maloney, Kevin M. ;

Kuethe, Jeffrey T. ;

Linn, Kathleen .

ORGANIC LETTERS, 2011, 13 (01) :102-105

[22] A Graphical Journey of Innovative Organic Architectures That Have Improved Our Lives [J].

McGrath, Nicholas A. ;

Brichacek, Matthew ;

Njardarson, Jon T. .

JOURNAL OF CHEMICAL EDUCATION, 2010, 87 (12) :1348-1349

[23] An approach toward the synthesis of β-hydroxy sulfones on water [J].

Murthy, S. Narayana ;

Madhav, B. ;

Reddy, V. Prakash ;

Rao, K. Rama ;

Nageswar, Y. V. D. .

TETRAHEDRON LETTERS, 2009, 50 (35) :5009-5011

[24] Diarylsulfones, a novel class of human immunodeficiency virus type 1 integrase inhibitors [J].

Neamati, N ;

Mazumder, A ;

Zhao, H ;

Sunder, S ;

Burke, TR ;

Schultz, RJ ;

Pommier, Y .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1997, 41 (02) :385-393

[25] Palladium-Catalyzed Aminosulfonylation of Aryl Halides [J].

Nguyen, Bao ;

Emmett, Edward J. ;

Willis, Michael C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (46) :16372-16373

[26] Sulfonamides identified as plant immune-priming compounds in high-throughput chemical screening increase disease resistance in Arabidopsis thaliana [J].

Noutoshi, Yoshiteru ;

Ikeda, Mika ;

Saito, Tamio ;

Osada, Hiroyuki ;

Shirasu, Ken .

FRONTIERS IN PLANT SCIENCE, 2012, 3

[27] Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans-synthesis and biological activity of new 2,4-diaminopyrimidines and 4′-substituted 4-aminodiphenyl sulfones [J].

Otzen, T ;

Wempe, EG ;

Kunz, B ;

Bartels, R ;

Lehwark-Yvetot, G ;

Hänsel, W ;

Schaper, KJ ;

Seydel, JK .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (01) :240-253

[28] One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation [J].

Richards-Taylor, Charlotte S. ;

Blakemore, David C. ;

Willis, Michael C. .

CHEMICAL SCIENCE, 2014, 5 (01) :222-228

[29] 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

[30] Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions [J].

Sato, K ;

Hyodo, M ;

Aoki, M ;

Zheng, XQ ;

Noyori, R .

TETRAHEDRON, 2001, 57 (13) :2469-2476

← 1 2 3 4 5 6 →