Issue 18, 2023

Visible-light-induced defluorinative allylation of difluoromethyl ketones using alkylamines as bifunctional agents

Abstract

A visible-light-induced alkylamine-facilitated reductive defluoroallylation of difluoromethyl ketones with allylic chlorides is reported, enabling efficient access to α-fluoro alkenylketones with high efficiency under catalyst-free and mild conditions. In this reaction, alkyl amines function as bifunctional agents: an electron donor for forming an electron donor–acceptor complex to trigger the selective C–F bond cleavage of CF2H-ketones and a halogen-atom transfer agent for activating the C–Cl bond of allylic chlorides. This protocol exhibits a broad substrate scope of CF2H-ketones and allylic halides. Synthetic derivatizations of the resulting α-fluoro alkenylketones and preliminary mechanistic studies have been presented.

Graphical abstract: Visible-light-induced defluorinative allylation of difluoromethyl ketones using alkylamines as bifunctional agents

Supplementary files

Article information

Article type
Research Article
Submitted
10 jun 2023
Accepted
13 aug 2023
First published
14 aug 2023

Org. Chem. Front., 2023,10, 4542-4549

Visible-light-induced defluorinative allylation of difluoromethyl ketones using alkylamines as bifunctional agents

X. Jiao, Z. Huang, W. Meng, S. Zhu and L. Chu, Org. Chem. Front., 2023, 10, 4542 DOI: 10.1039/D3QO00870C

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