Aqueous pulsed electrochemistry promotes C−N bond formation via a one-pot cascade approach

Meng He, Yongmeng Wu (), Rui Li, Yuting Wang, Cuibo Liu and Bin Zhang ()
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Meng He: Tianjin University
Yongmeng Wu: Tianjin University
Rui Li: Tianjin University
Yuting Wang: Tianjin University
Cuibo Liu: Tianjin University
Bin Zhang: Tianjin University

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: Abstract Electrocatalytic C − N bond formation from inorganic nitrogen wastes is an emerging sustainable method for synthesizing organic amines but is limited in reaction scope. Integrating heterogeneous and homogeneous catalysis for one-pot reactions to construct C − N bonds is highly desirable. Herein, we report an aqueous pulsed electrochemistry-mediated transformation of nitrite and arylboronic acids to arylamines with high yields. The overall process involves nitrite electroreduction to ammonia over a Cu nanocoral cathode and subsequent coupling of NH3 with arylboronic acids catalyzed by in situ dissolved Cu(II) under a switched anodic potential. This pulsed protocol also promotes the migration of nucleophilic ArB(OH)3− and causes the consumption of OH− near the cathode surface, accelerating C − N formation and suppressing phenol byproducts. Cu(II) can be recycled via facile electroplating. The wide substrate scope, ready synthesis of 15N-labelled arylamines, and methodological expansion to cycloaddition and Click reactions highlight the great promise.

Date: 2023
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DOI: 10.1038/s41467-023-40892-9

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