A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

Andrew D. Gillie; Matthew G. Wakeling; Bethan L. Greene; Louise Male; Paul W. Davies

doi:10.3762/bjoc.20.54

Beilstein Journal of Organic Chemistry (Mar 2024)

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

Andrew D. Gillie,
Matthew G. Wakeling,
Bethan L. Greene,
Louise Male,
Paul W. Davies

Affiliations

Andrew D. Gillie: School of Chemistry, University of Birmingham, Birmingham, B15 2TT, UK
Matthew G. Wakeling: School of Chemistry, University of Birmingham, Birmingham, B15 2TT, UK
Bethan L. Greene: School of Chemistry, University of Birmingham, Birmingham, B15 2TT, UK
Louise Male: School of Chemistry, University of Birmingham, Birmingham, B15 2TT, UK
Paul W. Davies: School of Chemistry, University of Birmingham, Birmingham, B15 2TT, UK

DOI: https://doi.org/10.3762/bjoc.20.54
Journal volume & issue: Vol. 20, no. 1
pp. 621 – 627

Abstract

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A polysubstituted 3-aminoimidazo[5,1-b]oxazol-6-ium framework has been accessed from a new nitrenoid reagent by a two-step ynamide annulation and imidazolium ring-formation sequence. Metalation with Au(I), Cu(I) and Ir(I) at the C2 position provides an L-shaped NHC ligand scaffold that has been validated in gold-catalysed alkyne hydration and arylative cyclisation reactions.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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