Download PDF
Synthesis 2024; 56(15): 2392-2402
DOI: 10.1055/s-0040-1720112
paper

Palladium-Catalyzed Amino-Sulfonylation of Aryl Iodide Derivatives via the Insertion of Sulfur Dioxide: One-Pot Synthesis of Aryl Primary Sulfonamides with Thiourea Dioxides

Panyu Ge
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
,
Ziyi Zhou
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
,
Jiahao Tao
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
,
Wei Cai
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
,
Minqin Wu
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
,
Xinggang Shan
b   Keyi college of Zhejiang Sci-Tech University, Shaoxing 312369, P. R. of China
,
Yong Li∗
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
,
Kai Cheng  ∗
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
› Author AffiliationsThis work was Supported by the Zhejiang Provincial Natural Science Foundation of China (No. LY18B020006), the National Natural Science Foundation of China (No. 21402123), the Research Project of Keyi College of Zhejiang Sci-Tech University (KY2021001) and the Department of Education of Zhejiang Province (No. Y202248464).
› Further Information
   Buy Article Permissions and Reprints All articles of this category


Zoom Image

Abstract

A palladium-catalyzed one-pot amino-sulfonylation of aryl iodide derivatives with thiourea dioxide, PdCl2dppf, and one-pot added hydroxylamine-O-sulfonic acid is presented. This amino-sulfonylation gave structure diversity to aryl primary sulfonamides and features good functional group compatibility, mild reaction conditions, excellent regioselectivity, and moderate to good yields. The robustness and potential of this method have also been successfully demonstrated by late-stage elaboration and gram-scale reaction. This approach achieves the divergent construction of the complex core structures that are prevalent in highly valuable natural products such as Sulpiride, Venetoclax, and Furosemide­.

Key words

Pd-catalyzed amino-sulfonylation - one-pot synthesis - aryl primary sulfonamide - thiourea dioxides

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720112.
  • Supporting Information


Publication History

Received: 24 October 2023

Accepted after revision: 26 March 2024

Article published online:
10 June 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany