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Electrochemical Access to Aza‐Polycyclic Aromatic Hydrocarbons: Rhoda‐Electrocatalyzed Domino Alkyne Annulations
Author(s) -
Kong WeiJun,
Shen Zhigao,
Finger Lars H.,
Ackermann Lutz
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201914775
Subject(s) - alkyne , regioselectivity , domino , chemistry , annulation , combinatorial chemistry , rhodium , functional group , cascade reaction , catalysis , organic chemistry , polymer
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.