通过 1,5-氢原子转移参与的炔烃二官能化和 C-N 裂解，光氧化催化合成 3,3-二氟-γ-内酰胺

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-08 DOI:10.1021/acs.orglett.4c03715

Lin Tang, Fengjuan Jia, Ge Lv, Xiaoyu Wang, Qiuju Zhou

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引用次数: 0

摘要

本手稿介绍了 1,5-氢原子转移策略在光氧化催化炔烃氢二氟烷基化中的应用。该方法利用二氟烷基化、1,5-氢原子转移、C(sp3)-N 裂解和分子内缩合环化的顺序级联过程，实现了易于获得的丙炔胺与卤代二氟乙酸酯（或卤代二氟乙酰胺）的高效[3 + 2]环加成。该反应可选择性地构建具有良好官能团耐受性的多取代 3,3-二氟-γ-内酰胺，还可将生成的 3,3-二氟-γ-内酰胺进一步转化为不同的构建基块。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Photoredox-Catalyzed Synthesis of 3,3-Difluoro-γ-lactams via 1,5-Hydrogen Atom Transfer-Involved Alkyne Difunctionalization and C–N Cleavage

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Photoredox-Catalyzed Synthesis of 3,3-Difluoro-γ-lactams via 1,5-Hydrogen Atom Transfer-Involved Alkyne Difunctionalization and C–N Cleavage

This manuscript describes the application of a 1,5-hydrogen atom transfer strategy in photoredox-catalyzed hydrodifluoroalkylation of alkynes. The approach utilizes a sequential cascade process of difluoroalkylation, 1,5-hydrogen atom transfer, C(sp³)–N cleavage, and intramolecular condensation cyclization to accomplish efficient [3 + 2] cycloaddition of readily available propargylamines with halodifluoroacetates (or halodifluoroacetamides). The reaction allows for the selective construction of polysubstituted 3,3-difluoro-γ-lactams with good functional group tolerance, and further transformations of the resulting 3,3-difluoro-γ-lactams into different building blocks are also accomplished.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.