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

Synthesis Pub Date : 2024-06-10 DOI:10.1055/s-0040-1720112
Panyu Ge, Ziyi Zhou, Jiahao Tao, Wei Cai, Minqin Wu, Xinggang Shan, Yong Li, Kai Cheng
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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.

Abstract Image

钯催化下通过插入二氧化硫对芳基碘化物衍生物进行氨基磺化反应:芳基伯磺酰胺与硫脲二氧杂环的一步法合成
本文介绍了钯催化的芳基碘化衍生物与二氧化硫脲、PdCl2dppf 和一次性添加的羟胺-O-磺酸的一次性氨基磺酰化反应。这种氨基磺化反应使芳基伯磺酰胺具有结构多样性,并具有良好的官能团兼容性、温和的反应条件、优异的区域选择性和中等至良好的收率。这种方法的稳健性和潜力也通过后期阐述和克级反应得到了成功验证。这种方法可实现复杂核心结构的发散构建,而这种结构在舒必利、维尼妥类和呋塞米等高价值天然产品中非常普遍。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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