Photoredox-Catalyzed Synthesis of N-Aryl γ-Lactams via Radical Addition–Cyclization Cascade

Synthesis Pub Date : 2024-08-28 DOI:10.1055/a-2378-8663
Aznur Azim, Vidhul Vasudevan, Tanumoy Mandal, Suman De Sarkar
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Abstract

A visible-light mediated one-pot synthesis of N-aryl γ-lactams is developed following a cascade radical addition/cyclization sequence. This transition metal-free approach proceeds efficiently at room temperature, employing an organic dye as the photocatalyst. Inexpensive N-arylglycines and acrylic acid derivatives were used as the starting materials and a vast array of diversely substituted N-aryl γ-lactams were synthesized in moderate to excellent yields. Detailed mechanistic experiments and comprehensive photophysical studies elucidated a plausible reaction mechanism.

Abstract Image

光氧化催化下通过自由基加成-环化级联合成 N-芳基 γ-内酰胺
通过级联自由基加成/环化顺序,开发了一种可见光介导的 N-芳基 γ-内酰胺的一锅合成方法。这种不含过渡金属的方法采用有机染料作为光催化剂,可在室温下高效进行。该方法以价格低廉的 N-芳基甘氨酸和丙烯酸衍生物为起始原料,合成了大量不同取代度的 N-芳基 γ-内酰胺,产率从中等到极佳。详细的机理实验和全面的光物理研究阐明了合理的反应机理。
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