Issue 5, 2024

Photoredox- and piezo-catalysed access to complex trifluoromethylated polycyclic structures from ynamides

Abstract

Radical cyclization cascades triggered by a trifluoromethyl radical represent a valuable tool for accessing highly complex and biologically relevant scaffolds. Herein, we introduce a strategy employing ynamides as pivotal functions for the diastereoselective synthesis of γ-lactam polycyclic compounds incorporating a trifluoromethyl group. Using photoredox conditions, this cascade featuring notably a 1,5 hydrogen atom transfer proceeds with high efficiency and diastereoselectivity. Additionally, a mechanoredox approach utilizing piezocatalysis proved to be competent in providing the same highly functionalized polycyclic products.

Graphical abstract: Photoredox- and piezo-catalysed access to complex trifluoromethylated polycyclic structures from ynamides

Supplementary files

Article information

Article type
Research Article
Submitted
06 Dec 2023
Accepted
27 Dec 2023
First published
03 Jan 2024

Org. Chem. Front., 2024,11, 1341-1349

Photoredox- and piezo-catalysed access to complex trifluoromethylated polycyclic structures from ynamides

A. Lakhal, M. Villeneuve, L. Haberkorn, J. Fourquez, J. Forte, G. Gontard, L. Fensterbank and C. Ollivier, Org. Chem. Front., 2024, 11, 1341 DOI: 10.1039/D3QO02016A

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