Issue 12, 2023

Aminals as powerful XAT-reagents: activation of fluorinated alkyl chlorides

Abstract

Readily available 1,3,5-trimethyl-1,3,5-triazinane serves as an efficient reagent for halogen atom transfer. Under photocatalytic conditions, the triazinane generates an α-aminoalkyl radical, which can activate the C–Cl bond of fluorinated alkyl chlorides. The hydrofluoroalkylation reaction between fluorinated alkyl chlorides and alkenes is described. The efficiency of the diamino-substituted radical derived from the triazinane is associated with stereoelectronic effects defined by a six-membered cycle forcing the anti-periplanar arrangement of the radical orbital and lone pairs of adjacent nitrogen atoms.

Graphical abstract: Aminals as powerful XAT-reagents: activation of fluorinated alkyl chlorides

Supplementary files

Article information

Article type
Edge Article
Submitted
03 Jan 2023
Accepted
20 Feb 2023
First published
21 Feb 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 3229-3234

Aminals as powerful XAT-reagents: activation of fluorinated alkyl chlorides

V. S. Kostromitin, A. O. Sorokin, Vitalij V. Levin and A. D. Dilman, Chem. Sci., 2023, 14, 3229 DOI: 10.1039/D3SC00027C

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