N-Heterocyclic Carbene Catalysis Exploiting Oxidative Imine Umpolung for the Generation of Imidoyl Azoliums

Das, TK and Madica, K and Krishnan, J and Marelli, UK and Biju, AT (2020) N-Heterocyclic Carbene Catalysis Exploiting Oxidative Imine Umpolung for the Generation of Imidoyl Azoliums. In: Journal of Organic Chemistry, 85 (7). pp. 5114-5121.

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Abstract

Although NHC-catalyzed umpolung of imines are known, the related reactions under oxidative conditions are limited. Described herein is the two-step process involving the initial formation of aldimines from the corresponding aldehydes and 2-amino benzyl alcohols followed by NHC-catalyzed cyclization proceeding via the imidoyl azoliums under oxidative conditions. The reaction allowed the synthesis of trifluoromethylated 3,1-benzoxazines in good yields and broad scope. The role of NHC in the intramolecular cyclization and preliminary mechanistic experiments are also provided. Copyright © 2020 American Chemical Society.

Item Type:	Journal Article
Publication:	Journal of Organic Chemistry
Publisher:	AMER CHEMICAL SOC
Additional Information:	The copyright of this article belongs to AMER CHEMICAL SOC
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	11 Aug 2020 09:23
Last Modified:	11 Aug 2020 09:23
URI:	http://eprints.iisc.ac.in/id/eprint/65354

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