Issue 4, 2023

Fluoroamide-driven intermolecular hydrogen-atom-transfer-enabled intermolecular 1,2-alkylarylation of alkenes

Abstract

A new fluoroamide-driven intermolecular hydrogen atom transfer (HAT) strategy for the copper-catalyzed intermolecular 1,2-alkylarylation of alkenes with carbazates and various arene nucleophiles, such as indoles, pyrroles and 1,3,5-trimethoxybenzene, is described. By using N-(tert-butyl)-N-fluoro-3,5-bis(trifluoromethyl)benzenesulfonamide (NFBS) as the intermolecular HAT reagent, this reaction enables the generation of carbazate nitrogen-centered radicals through intermolecular HAT followed by decomposition to form alkyl radicals, radical addition across the alkene, single electron oxidation and nucleophilic coupling cascades to achieve the alkene 1,2-alkylarylation.

Graphical abstract: Fluoroamide-driven intermolecular hydrogen-atom-transfer-enabled intermolecular 1,2-alkylarylation of alkenes

Supplementary files

Article information

Article type
Research Article
Submitted
07 Oct 2022
Accepted
26 Nov 2022
First published
28 Nov 2022

Org. Chem. Front., 2023,10, 943-950

Fluoroamide-driven intermolecular hydrogen-atom-transfer-enabled intermolecular 1,2-alkylarylation of alkenes

C. Cheng, D. Chen, Y. Li, J. Xiang and J. Li, Org. Chem. Front., 2023, 10, 943 DOI: 10.1039/D2QO01580C

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