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

被引：211

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

[1]

[Anonymous], 2014, ANGEW CHE

[2]

[Anonymous], 2014, ANGEW CHEM

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

Chen, C. Chun ;

Waser, Jerome .

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

[4] Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes [J].

Crowley, PJ ;

Fawcett, J ;

Kariuki, BM ;

Moralee, AC ;

Percy, JM ;

Salafia, V .

ORGANIC LETTERS, 2002, 4 (23) :4125-4128

[5] 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

[6]

Deeming A. S., 2014, SYNTHESIS-STUTTGART, P2701

[7] 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

[8] 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

[9] 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

[10] Palladium-Catalyzed Synthesis of Ammonium Sulfinates from Aryl Halides and a Sulfur Dioxide Surrogate: A Gas- and Reductant-Free Process [J].

Emmett, Edward J. ;

Hayter, Barry R. ;

Willis, Michael C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) :10204-10208

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