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Synthesis 2024; 56(15): 2392-2402
DOI: 10.1055/s-0040-1720112
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
This 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).
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 dioxidesSupporting 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
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