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

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.

SUBMITTER: He M 

PROVIDER: S-EPMC10444869 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature