Issue 1, 2024

Photoredox-catalyzed intramolecular oxy- and aminoacylation of alkenes with acyl oxime esters: facile synthesis of acylated saturated heterocycles

Abstract

In the present paper, an efficient photoredox-catalyzed intramolecular oxy- and aminoacylation of internal alkenes equipped with pendant oxygen- or nitrogen-centered nucleophiles with acyl oxime esters is reported. Under visible-light irradiation, a variety of structurally diverse acylated saturated heterocycles, such as tetrahydrofurans, tetrahydropyrans, δ-valerolactones, tetrahydropyrroles, piperidines, tetrahydro-1,3-oxazepines, etc., were efficiently synthesized from easily accessible unsaturated alcohols, carboxylic acids, tosyl-protected amines, and O-homoallyl benzimidates via an acyl radical-mediated cascade acylation/cyclization process. This light-driven transformation features a broad substrate scope, good functional group compatibility, high regio- and diastereoselectivity, and mild reaction conditions, representing a general and practical procedure toward the construction of acylated saturated heterocycles as well as their derivatives.

Graphical abstract: Photoredox-catalyzed intramolecular oxy- and aminoacylation of alkenes with acyl oxime esters: facile synthesis of acylated saturated heterocycles

Supplementary files

Article information

Article type
Research Article
Submitted
09 Oct 2023
Accepted
07 Nov 2023
First published
17 Nov 2023

Org. Chem. Front., 2024,11, 74-82

Photoredox-catalyzed intramolecular oxy- and aminoacylation of alkenes with acyl oxime esters: facile synthesis of acylated saturated heterocycles

X. Mou, M. Wang, L. Ren, Y. Jian, X. Fu, H. Zheng, X. Zha, B. Cui, Y. Zhang and Y. Chen, Org. Chem. Front., 2024, 11, 74 DOI: 10.1039/D3QO01659E

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