Synthesis
DOI: 10.1055/a-2378-8663
paper
Special Topic Dedicated to Prof. H. Ila

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

Aznur Azim
,
Vidhul Vasudevan
,
Tanumoy Mandal
,
Generous support by the CSIR [fellowship to AA, TM and 02(0407)/21/EMR-II to SDS] and IISER Kolkata and DST-INSPIRE (for fellowship to VV and infrastructure) is gratefully acknowledged.


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.

Supporting Information



Publication History

Received: 27 June 2024

Accepted after revision: 02 August 2024

Accepted Manuscript online:
02 August 2024

Article published online:
28 August 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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