Issue 22, 2022

General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides

Abstract

Herein, we report, a general, facile and environmentally friendly Minisci-type alkylation of N-heteroarenes under simple and straightforward electrochemical conditions using widely available alkyl halides as radical precursors. Primary, secondary and tertiary alkyl radicals have been shown to be efficiently generated and coupled with a large variety of N-heteroarenes. The method presents a very high functional group tolerance, including various heterocyclic-based natural products, which highlights the robustness of the methodology. This applicability has been further proved in the synthesis of various interesting biologically valuable building blocks. In addition, we have proposed a mechanism based on different proofs and pieces of electrochemical evidence.

Graphical abstract: General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides

Supplementary files

Article information

Article type
Edge Article
Submitted
29 mar. 2022
Accepted
26 apr. 2022
First published
06 maí 2022
This article is Open Access

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

Chem. Sci., 2022,13, 6512-6518

General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides

R. D. Río-Rodríguez, L. Fragoso-Jarillo, A. F. Garrido-Castro, M. C. Maestro, J. A. Fernández-Salas and J. Alemán, Chem. Sci., 2022, 13, 6512 DOI: 10.1039/D2SC01799G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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