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Oxidative NHC Catalysis for the Generation of Imidoyl Azoliums: Synthesis of Benzoxazoles

Atanu Patra, Anjima James, Tamal Kanti Das, Akkattu T. Biju*

*Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India, Email: atbijuiisc.ac.in

A. Patra, A. James, T. K. Das, A. T. Biju, J. Org. Chem., 2018, 83, 14820-14826.

DOI: 10.1021/acs.joc.8b02598 (free Supporting Information)


Abstract

A N-heterocyclic carbene (NHC)-catalyzed intramolecular cyclization of aldimines generated from 2-amino phenols and aromatic aldehydes provides 2-arylbenzoxazoles in good yields under mild conditions. The reaction tolerates a broad range of functional groups.

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proposed mechanism



Key Words

benzoxazoles, DPQ, organocatalysis


ID: J42-Y2018