Selective Synthesis of ortho-Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions

Haibo Zhu; Yajing Shen; Daheng Wen; Zhang-Gao Le; Tao Tu

doi:10.1021/acs.orglett.8b03957

Selective Synthesis of ortho-Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions

Org Lett. 2019 Feb 15;21(4):974-979. doi: 10.1021/acs.orglett.8b03957. Epub 2019 Jan 31.

Authors

Haibo Zhu^{1

2}, Yajing Shen¹, Daheng Wen¹, Zhang-Gao Le², Tao Tu^{1

3}

Affiliations

¹ Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Department of Chemistry , Fudan University , 2205 Songhu Road , Shanghai 200438 , China.
² School of Chemistry, Biology and Material Science , East China University of Technology , Nanchang 330013 , China.
³ State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , Shanghai 200032 , China.

PMID: 30702302
DOI: 10.1021/acs.orglett.8b03957

Abstract

A single-step gold(I)-catalyzed chemoselective protocol to access ortho-substituted diarylsulfones has been established. Acenaphthoimidazolylidene gold complexes are effective catalysts for the arylsulfonylation of boronic acids by potassium metabisulfite (K₂S₂O₅) and diaryliodonium salts to access (poly-) ortho-substituted diarylsulfones even in gram scale. Unlike the transition metal-catalyzed two-component coupling systems, the sterically hindered aryl groups in diaryliodonium salts are preferentially transferred over less bulky ones to form synthetically difficult targets, including those of pharmaceutical importance.

Publication types

Research Support, Non-U.S. Gov't