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

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...

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Bibliographic Details
Published in:Organic letters 2023-06, Vol.25 (22), p.4010-4015
Main Authors: Vázquez-Amaya, Laura Y., Dootselaere, Brecht, Ojeda-Carralero, Gerardo M., Pillitteri, Serena, Van der Eycken, Johan, Van der Eycken, Erik V., Sharma, Upendra K.
Format: Article
Language:English
Subjects:
Alkylating Agents
Amines
Boronic Acids
Imines
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01020