4.8 Article

Mn-Catalyzed Electrochemical Radical Cascade Cyclization toward the Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one Derivatives

Journal

ACS CATALYSIS
Volume 10, Issue 12, Pages 6676-6681

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c01324

Keywords

electrochemistry; radical cascade cyclization; alkylboronic acids; benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives; hydrogen evolution

Funding

  1. Jiangxi Normal University
  2. National Natural Science Foundation of China [21520102003]
  3. Hubei Province Natural Science Foundation of China [2017CFA010]
  4. Program of Introducing Talents of Discipline to Universities of China (111 Program)

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Benzo [4,5] imidazo [2,1-a]isoquinolin-6(5H)- one derivatives are prevalent in many synthetic intermediates, pharmaceuticals, and organic materials. Herein, we develop a Mn-catalyzed electrochemical radical cascade cyclization reaction that uses electricity as the primary energy input to promote the reaction, leading to a series of benzo[4,5]imidazo[2,1-a]- isoquinolin-6(5H)-one derivatives under exogenous-oxidant-free conditions. It is worth noting that this electrochemical method can not only realize the synthesis of benzo 4,5 imidazo[2,1- a]isoquinolin-6(5H)-one derivatives but also provides a new strategy for generating alkyl radicals from alkylboronic acids.

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