An IEDDA Reaction of Propargyl Sulfonium Salts and Tetrazines： A Versatile [4+2] Modular Assembly

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-10-01 DOI:10.1039/d5qo01092f

Jiaan Shao, Zheng Wang, Qi Zhu, Jiankang Zhang, Huajian Zhu, Wenteng Chen

引用次数: 0

Abstract

The propargyl sulfonium salt has been reported as a novel electronrich olefin precursor that undergoes an inverse electron-demand Diels-Alder [4+2] reaction with tetrazines. This method enables the rapid and modular assembly of structurally diverse propargyl sulfonium salts and tetrazines, offering significant features such as short reaction time, excellent efficiency, and mild reaction conditions. Notably, this approach has been further extended to propargyl sulfonium-peptide systems for the site-specific labeling of methionine residues in short peptides and the construction of cyclic peptides.

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丙炔磺酸盐和四嗪的IEDDA反应：一个通用的[4+2]模块组装

丙炔磺酸盐是一种新的富电子烯烃前驱体，与四嗪发生逆电按需Diels-Alder[4+2]反应。该方法能够快速、模块化地组装结构多样的丙炔磺酸盐和四嗪，具有反应时间短、效率高、反应条件温和等显著特点。值得注意的是，这种方法已进一步扩展到丙炔磺酸-肽系统，用于短肽中蛋氨酸残基的位点特异性标记和环肽的构建。

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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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.