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

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

doi:10.1002/asia.201601732

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

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

Authors

Haibo Zhu¹, Yajing Shen¹, Qinyue Deng¹, Changyu Huang¹, Tao Tu^{1

2}

Affiliations

¹ Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.

PMID: 28079985
DOI: 10.1002/asia.201601732

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.

Keywords: boronic acids; copper; o-benzoyl hydroxylamines; palladium; sulfonamides.