Gold-Mediated Cyclization of N-Acrylamides via Energy Transfer Photocatalysis

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-26 DOI:10.1021/acs.orglett.4c03919

Yuan Zhao, Sébastien G. Guillet, Vladislav A. Voloshkin, Steven P. Nolan

引用次数: 0

Abstract

We disclose a gold-mediated photocyclization method for the efficient synthesis of acrylamide-derived β-lactams and 3,4-dihydroquinolin-2-ones, two privileged bioactive scaffolds. The protocol proceeds with ease, providing good yields of product while exhibiting excellent functional group tolerance at low catalyst loadings in sustainable solvents. Additionally, reaction times are significantly reduced compared with prior-art methods. Notably, the present gold system exhibits superior performance in activating poorly conjugated substrates, which are typically unreactive with other photocatalysts, highlighting the exceptional position of this organogold system among modern photocatalysts.

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通过能量转移光催化技术实现金介导的 N-丙烯酰胺环化反应

我们公开了一种金介导的光环化方法，用于高效合成丙烯酰胺衍生的 β-内酰胺和 3,4-二氢喹啉-2-酮这两种具有特殊生物活性的支架。该方法简单易行，在可持续溶剂中以较低的催化剂载量即可获得高产率的产品，同时还表现出优异的官能团耐受性。此外，与之前的方法相比，反应时间大大缩短。值得注意的是，这种金体系在活化通常与其他光催化剂不发生反应的低共轭基质方面表现出卓越的性能，突出了这种有机金体系在现代光催化剂中的特殊地位。

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 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.