Issue 20, 2024

Copper-catalyzed oxidative dehydrogenative [3 + 2] annulation of oximes with α-amino ketones: entry to 3-aminopyrroles

Abstract

An unprecedented copper-catalyzed oxidative dehydrogenative [3 + 2] annulation of O-acyl oximes containing α-C(sp3)–H bonds with α-amino ketones for the preparation of 3-aminopyrroles is developed. This method uses O-acyl oximes as both internal oxidants and three-atom-unit components combined with the copper catalyst to drive catalytically generated oxime nitrogen-centered radicals and oxidative dehydrogenation of the α-amino ketones to form the key 2-iminoethan-1-one intermediates, enabling site-selective cleavage of the multiple α-C(sp3)–H bonds in O-acyl oximes and α-amino ketones to create two new bonds, including a C(sp2)–C(sp2) bond and a C(sp2)–N bond, between the carbon atoms and the nitrogen atom in a cross-selective fashion.

Graphical abstract: Copper-catalyzed oxidative dehydrogenative [3 + 2] annulation of oximes with α-amino ketones: entry to 3-aminopyrroles

Supplementary files

Article information

Article type
Research Article
Submitted
16 Jul 2024
Accepted
22 Aug 2024
First published
23 Aug 2024

Org. Chem. Front., 2024,11, 5806-5812

Copper-catalyzed oxidative dehydrogenative [3 + 2] annulation of oximes with α-amino ketones: entry to 3-aminopyrroles

Y. Liu, M. Hu and J. Li, Org. Chem. Front., 2024, 11, 5806 DOI: 10.1039/D4QO01307G

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