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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.

SUBMITTER: Del Rio-Rodriguez R

PROVIDER: S-EPMC9172443 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides.

Del Río-Rodríguez Roberto R Fragoso-Jarillo Lorena L Garrido-Castro Alberto F AF Maestro M Carmen MC Fernández-Salas Jose A JA Alemán José J

Chemical science 20220506 22

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, ...[more]

PMID: 35756520

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