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 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.

Авторы
Vázquez-Amaya Laura Y.1 , Dootselaere Brecht1 , Ojeda-Carralero Gerardo M.2 , Pillitteri Serena1 , Van der Eycken Johan3 , Van der Eycken Erik V. 1, 4 , Sharma Upendra K.1
Журнал
Номер выпуска
22
Язык
Английский
Страницы
4010-4015
Статус
Опубликовано
Том
25
Год
2023
Организации
  • 1 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium
  • 2 Department of General and Inorganic Chemistry, Faculty of Chemistry, University of Havana, Zapata y G, Havana 10400, Cuba
  • 3 Laboratory for Organic and Bio-Organic Synthesis, Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 (S.4), B-9000 Ghent, Belgium
  • 4 People’s Friendship University of Russia (RUDN University), Miklukho-Maklaya street 6, RU-117198 Moscow, Russia
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