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Light-Driven Four-Component Reaction with Boronic Acid Derivatives as Alkylating Agents: An Amine/Imine-Mediated Activation Approach

Laura Y. Vázquez-Amaya, Brecht Dootselaere, Gerardo M. Ojeda‐Carralero, Serena Pillitteri, Johan Van der Eycken, Erik V. Van der Eycken, Upendra K. Sharma

2023Organic Letters18 citationsDOIOpen Access PDF

Abstract

Herein, we describe a one-pot aminoalkylation of styrene derivatives with boronic acids (BAs) and boronic acid pinacol esters as radical precursors for the synthesis of complex secondary amines in moderate to high yields through a mild and easily accessible organophotoredox-catalytic four-component reaction. Additionally, we report for the first time in a photoredox process the activation of alkyl boronic acid derivatives by imines, which play a dual role in the reaction as both substrate and Lewis base activator. The protocol applicability was greatly enhanced by its successful adaptation to photoflow reactors.

Topics & Concepts

ChemistryPinacolBoronic acidAmine gas treatingStyreneAlkylImineCombinatorial chemistryLewis acids and basesCatalysisOrganic chemistryCopolymerPolymerRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods
Light-Driven Four-Component Reaction with Boronic Acid Derivatives as Alkylating Agents: An Amine/Imine-Mediated Activation Approach | Litcius