光氧化催化烯与β-内酰胺的分子内亲核酰胺化反应。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2024-10-01 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.210

Valentina Giraldi, Giandomenico Magagnano, Daria Giacomini, Pier Giorgio Cozzi, Andrea Gualandi

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引用次数: 0

摘要

通过光氧化催化将酰胺与未官能化的烯烃直接进行亲核加成是实现官能化烷基酰胺的一种简便方法。遗憾的是，酰胺的亲核性不足以及竞争性副反应限制了这种方法的实用性。在此，我们报告了在吖啶光催化剂存在下烯与β-内酰胺的分子内光氧化环化反应。该方法利用 β-内酰胺氮原子与连接的烯分子中光生成的自由基阳离子进行分子内亲核加成，然后通过氢原子转移催化剂进行氢转移。利用这一过程成功制备了 2-烷基化克拉维姆衍生物。

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Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams.

The direct nucleophilic addition of amides to unfunctionalized alkenes via photoredox catalysis represents a facile approach towards functionalized alkylamides. Unfortunately, the scarce nucleophilicity of amides and competitive side reactions limit the utility of this approach. Herein, we report an intramolecular photoredox cyclization of alkenes with β-lactams in the presence of an acridinium photocatalyst. The approach uses an intramolecular nucleophilic addition of the β-lactam nitrogen atom to the radical cation photogenerated in the linked alkene moiety, followed by hydrogen transfer from the hydrogen atom transfer (HAT) catalyst. This process was used to successfully prepare 2-alkylated clavam derivatives.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.