n-磷硫代琥珀酰亚胺的亲电分子间卤代磷硫代和磷硫代脱芳化烯烃/炔

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-08-01 DOI:10.1039/d5qo00959f

Yuan Zhang, Mingyang Chen, Xu Chen, Xuesi Zhou, Yitai Fu, Xiang Liu, Hua Cao

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引用次数: 0

摘要

由于缺乏实用的亲电试剂，亲电性硫代磷酸化是一种有吸引力的策略，很少被探索。本研究以TMSX为活化剂和亲核卤素源，开发了亲电性硫代磷酸酯转移试剂，并揭示了其在灭活烯烃的亲电性分子间卤代硫代硫代化中的合成应用。此外，还实现了炔烃的磷硫代脱芳化，得到磷硫代螺[4,5]三烯酮。值得注意的是，所开发的方法成功地用于药物分子衍生物的后期修饰。

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Electrophilic Intermolecular Halo-Phosphorothiolation and Phosphorothiolation-Dearomatization of Alkenes/Alkynes with N-Phosphorothiosuccinimide

Electrophilic phosphorothiolations represent an attractive strategy that has been rarely explored due to the lack of practical electrophilic reagents. Herein, we developed electrophilic phosphorothioate transfer reagents and unveiled their synthetic application in the electrophilic intermolecular halo-phosphorothiolation of inactivated alkenes with TMSX as activator and nucleophilic halogen sources. In addition, phosphorothiolation-dearomatization of alkynes were also achieved to furnish phosphorothiolated spiro[4,5]trienones. Notably, the developed method is successfully employed for the late-stage modification of pharmaceutical molecule derivatives.

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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.