Issue 89, 2021

Cu-catalyzed C(sp2)–N-bond coupling of boronic acids and cyclic imides

Abstract

A general Cu-catalyzed strategy for coupling cyclic imides and alkenylboronic acids by forming C(sp2)N-bonds is reported. The method enables the practical and mild preparation of (E)-enimides. A large range of cyclic imides are allowed, and di- and tri-substituted alkenylboronic acids can be used. Full retention was observed in the configuration of the alkene double bond in the coupled products. The method is also applicable for preparing N-arylimides, using arylboronic acids as coupling partners. The usefulness of this strategy is exemplified by the convenient derivatization of the chemotherapy medication 5-flurouracil, the nucleoside uridine and the anti-epileptic drug phenytoin.

Graphical abstract: Cu-catalyzed C(sp2)–N-bond coupling of boronic acids and cyclic imides

Supplementary files

Article information

Article type
Communication
Submitted
09 Aug 2021
Accepted
19 Oct 2021
First published
19 Oct 2021
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2021,57, 11851-11854

Cu-catalyzed C(sp2)–N-bond coupling of boronic acids and cyclic imides

L. N. Berntsen, T. N. Solvi, K. Sørnes, D. S. Wragg and A. H. Sandtorv, Chem. Commun., 2021, 57, 11851 DOI: 10.1039/D1CC04356K

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