Zhang Xiaolong, Sivaguru Paramasivam, Pan Yongzhen, Wang Nan, Zhang Wenjie, Bi Xihe
Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Chem Rev. 2025 Jan 22;125(2):1049-1190. doi: 10.1021/acs.chemrev.4c00742. Epub 2025 Jan 10.
-Sulfonyl hydrazones have been extensively used as operationally safe carbene precursors in modern organic synthesis due to their ready availability, facile functionalization, and environmental benignity. Over the past two decades, there has been tremendous progress in the carbene chemistry of -sulfonyl hydrazones in the presence of transition metal catalysts, under metal-free conditions, or using photocatalysts under photoirradiation conditions. Many carbene transfer reactions of -sulfonyl hydrazones are unique and cannot be achieved by any alternative methods. The discovery of novel -sulfonyl hydrazones and the development of highly enantioselective new reactions and skeletal editing reactions represent the notable recent achievements in the carbene chemistry of -sulfonyl hydrazones. This review describes the overall progress made in the carbene chemistry of -sulfonyl hydrazones, organized based on reaction types, spotlighting the current state-of-the-art and remaining challenges to be addressed in the future. Special emphasis is devoted to identifying, describing, and comparing the scope and limitations of current methodologies, key mechanistic scenarios, and potential applications in the synthesis of complex molecules.
由于磺酰腙易于获得、易于官能化且环境友好，它们在现代有机合成中已被广泛用作操作安全的卡宾前体。在过去二十年中，在过渡金属催化剂存在下、无金属条件下或光照射条件下使用光催化剂时，磺酰腙的卡宾化学取得了巨大进展。许多磺酰腙的卡宾转移反应是独特的，无法通过任何其他方法实现。新型磺酰腙的发现以及高对映选择性新反应和骨架编辑反应的发展代表了磺酰腙卡宾化学最近的显著成就。本综述描述了磺酰腙卡宾化学取得的总体进展，按反应类型进行组织，突出了当前的技术水平以及未来有待解决的挑战。特别强调识别、描述和比较当前方法的范围和局限性、关键机理情况以及在复杂分子合成中的潜在应用。
