Scalable and Selective Electrochemical Hydrogenation of Polycyclic Arenes.

Angew Chem Int Ed Engl

The Institute for Advanced Studies (IAS), College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, Hubei, P. R. China.

Published: August 2024

AI Article Synopsis

  • The study focuses on the selective reduction of polycyclic aromatic compounds, which is a challenging process in chemistry, especially for complex molecules.
  • The researchers developed a new electrochemical hydrogenation method that allows for precise control of both complete and partial reductions of specific aromatic rings by adjusting the solvents used.
  • This method demonstrated high functional-group tolerance and scalability, successfully reducing a 1 kg starting material and producing important intermediates for drug synthesis.

Article Abstract

The reduction of aromatic compounds constitutes a fundamental and ongoing area of investigation. The selective reduction of polycyclic aromatic compounds to give either fully or partially reduced products remains a challenge, especially in applications to complex molecules at scale. Herein, we present a selective electrochemical hydrogenation of polycyclic arenes conducted under mild conditions. A noteworthy achievement of this approach is the ability to finely control both the complete and partial reduction of specific aromatic rings within polycyclic arenes by judiciously varying the reaction solvents. Mechanistic investigations elucidate the pivotal role played by in situ proton generation and interface regulation in governing reaction selectivity. The reductive electrochemical conditions show a very high level of functional-group tolerance. Furthermore, this methodology represents an easily scalable reduction (demonstrated by the reduction of 1 kg scale starting material) using electrochemical flow chemistry to give key intermediates for the synthesis of specific drugs.

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Source
http://dx.doi.org/10.1002/anie.202407392DOI Listing

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