Microwave-enhanced additive-free C–H amination of benzoxazoles catalysed by supported copper

The C2-amination of benzoxazole offers wide-ranging potential for substrate expansion and the functionalisation of bioactive compounds. This study presents a green and efficient C–H amination, catalysed by CuCl and CuCl2, in acetonitrile without acidic, basic or oxidant additives that is accelerated...

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Bibliographic Details
Main Authors: Andrei Paraschiv, Valentina Maruzzo, Filippo Pettazzi, Stefano Magliocco, Paolo Inaudi, Daria Brambilla, Gloria Berlier, Giancarlo Cravotto, Katia Martina
Format: Article
Language:English
Published: Beilstein-Institut 2025-07-01
Series:Beilstein Journal of Organic Chemistry
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Online Access:https://doi.org/10.3762/bjoc.21.108
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Summary:The C2-amination of benzoxazole offers wide-ranging potential for substrate expansion and the functionalisation of bioactive compounds. This study presents a green and efficient C–H amination, catalysed by CuCl and CuCl2, in acetonitrile without acidic, basic or oxidant additives that is accelerated by microwave (MW) irradiation and is completed in 1.5–2 h. A solid Cu(I) catalyst supported on aminated silica made the process cost-effective and heterogeneous, thus simplifying work-up and minimising free copper in solution. The catalyst was found to be regeneratable and reusable for up to eight cycles. The optimised method facilitated the synthesis of various benzoxazole derivatives, demonstrating its versatility and practical applicability.
ISSN:1860-5397