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

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