Abstract
Nitrogen‐doped polycyclic aromatic hydrocarbons (aza‐PAHs) have found broad applications in material sciences. Herein, a modular electrochemical synthesis of aza‐PAHs was developed via a rhodium‐catalyzed cascade C−H activation and alkyne annulation. A multifunctional O‐methylamidoxime enabled the high chemo‐ and regioselectivity. The isolation of two key rhodacyclic intermediates made it possible to delineate the exact order of three C−H activation steps. In addition, the metalla‐electrocatalyzed multiple C−H transformation is characterized by unique functional group tolerance, including highly reactive iodo and azido groups.
Highlights
Nitrogen-doped polycyclic aromatic hydrocarbons have found broad applications in material sciences
A modular electrochemical synthesis of azaPAHs was developed via a rhodium-catalyzed cascade CÀH activation and alkyne annulation
The isolation of two key rhodacyclic intermediates made it possible to delineate the exact order of three CÀH activation steps
Summary
Nitrogen-doped polycyclic aromatic hydrocarbons (aza-PAHs) have found broad applications in material sciences. A modular electrochemical synthesis of azaPAHs was developed via a rhodium-catalyzed cascade CÀH activation and alkyne annulation. The metalla-electrocatalyzed multiple CÀH transformation is characterized by unique functional group tolerance, including highly reactive iodo and azido groups.
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