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Electrochemically Enabled Chan–Lam Couplings of Aryl Boronic Acids and Anilines

Author:
Wexler, Ryan P., Nuhant, Philippe, Senter, Timothy J., Gale-Day, Zachary J.
Source:
Organic letters 2019 v.21 no.12 pp. 4540-4543
ISSN:
1523-7052
Subject:
Lewis bases, amines, anodes, boronic acids, cathodes, chemical bonding, chemical reactions, chemical structure, copper, electrochemistry
Abstract:
The Chan–Lam reaction remains a highly utilized transformation for C–N bond formation. However, anilines remain problematic substrates due to their lower nucleophilicity. To address this problem, we developed an electrochemically mediated Chan–Lam coupling of aryl boronic acids and amines utilizing a dual copper anode/cathode system. The mild conditions identified have enabled the preparation of a wide range of functionalized biarylanilines in good yields and chemoselectivities.
Agid:
6478167