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一锅法双金属钯/铜催化由硼酸、DABSO和O-苯甲酰羟胺合成磺酰胺

One-Pot Bimetallic Pd/Cu-Catalyzed Synthesis of Sulfonamides from Boronic Acids, DABSO and O-Benzoyl Hydroxylamines.

作者信息

Zhu Haibo, Shen Yajing, Deng Qinyue, Huang Changyu, Tu Tao

机构信息

Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.

出版信息

Chem Asian J. 2017 Mar 16;12(6):706-712. doi: 10.1002/asia.201601732. Epub 2017 Jan 31.

DOI:10.1002/asia.201601732
PMID:28079985
Abstract

A practical and straightforward bimetallic Pd/Cu catalytic system has been developed. This system affords various sulfonamides in one pot from easy-to-handle and readily available boronic acids, sulfur dioxide surrogate DABSO and O-benzoyl hydroxylamines in high yields. Without additional ligands, the newly developed catalytic system revealed a broad substrate scope for both partners and tolerated a wide array of functional groups even at low catalyst loadings. Furthermore, based on control experiments, a plausible mechanism has been proposed, in which sodium sulfinate has been isolated and identified as the crucial intermediate for this transformation.

摘要

已开发出一种实用且简单的双金属钯/铜催化体系。该体系能以高产率由易于操作且 readily available 的硼酸、二氧化硫替代物 DABSO 和 O-苯甲酰羟胺一锅法制备各种磺胺。在无额外配体的情况下,新开发的催化体系对两种反应物均显示出广泛的底物范围,即使在低催化剂负载量时也能耐受多种官能团。此外,基于对照实验,提出了一种合理的机理,其中亚磺酸钠已被分离并鉴定为该转化的关键中间体。

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