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Catalyst‐Free, Air‐Mediated C(<i>sp</i><sup>2</sup>)−H Alkylation of Cyclic Aldimines with Alkylboronic Acids

Jie Zhang, Xiaolan Li, Lieqiang Liao, Haidong Liu, Haiqing Luo

2023Advanced Synthesis & Catalysis12 citationsDOIOpen Access PDF

Abstract

Abstract The air mediated radical alkylation of cyclic aldimines via autoxidation of alkylboronic acids has been realized under mild reaction conditions. By simply heating cyclic aldimines with alkylboronic acid using air as sole oxidant, this protocol provides a catalyst‐free access to a variety of alkylated cyclic aldimines with 21–91% yields. Preliminary mechanistic studies suggest that a radical pathway might be involved in the reaction.

Topics & Concepts

AldimineChemistryAlkylationAutoxidationCatalysisOrganic chemistryReaction conditionsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions
Catalyst‐Free, Air‐Mediated C(<i>sp</i><sup>2</sup>)−H Alkylation of Cyclic Aldimines with Alkylboronic Acids | Litcius