Issue 33, 2023

Visible light-induced radical cascade acylmethylation/cyclization of 2-(allyloxy)arylaldehydes with α-bromo ketones: access to cyclic 1,5-dicarbonyl-containing chroman-4-one skeletons

Abstract

A novel photocatalytic protocol for effective and efficient synthesis of cyclic 1,5-diketones containing chroman-4-one skeletons in moderate to good yields via radical cascade acylmethylation/cyclization of 2-(allyloxy)arylaldehydes with α-bromo ketones has been described. This reaction features a broad substrate scope, good functional group tolerance, and metal- and oxidant-free conditions. An acylmethyl radical-triggered cascade cyclization was involved.

Graphical abstract: Visible light-induced radical cascade acylmethylation/cyclization of 2-(allyloxy)arylaldehydes with α-bromo ketones: access to cyclic 1,5-dicarbonyl-containing chroman-4-one skeletons

Supplementary files

Article information

Article type
Paper
Submitted
09 Jul 2023
Accepted
02 Aug 2023
First published
02 Aug 2023

Org. Biomol. Chem., 2023,21, 6772-6777

Visible light-induced radical cascade acylmethylation/cyclization of 2-(allyloxy)arylaldehydes with α-bromo ketones: access to cyclic 1,5-dicarbonyl-containing chroman-4-one skeletons

X. Huang, F. Liu, T. Fu, X. Hu, Y. Wang, B. Liu, M. Teng and G. Huang, Org. Biomol. Chem., 2023, 21, 6772 DOI: 10.1039/D3OB01101A

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