Synthesis of 2-Aryl Naphthoquinones by the Cross-Dehydrogenative Coupling Involving an NHC-Catalyzed endo-Stetter Reaction

Ghosh, A and Patra, A and Mukherjee, S and Biju, AT (2019) Synthesis of 2-Aryl Naphthoquinones by the Cross-Dehydrogenative Coupling Involving an NHC-Catalyzed endo-Stetter Reaction. In: Journal of Organic Chemistry, 84 (2). pp. 1103-1110.

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Abstract

An N-heterocyclic carbene (NHC)-catalyzed intramolecular Stetter reaction proceeding via the endo-fashion was the key step for the transition-metal-free and mild cross-dehydrogenative coupling of 2-cinnamoyl benzaldehydes allowing for the synthesis of 2-aryl naphthoquinones. In this transformation, the carbene generated from the triazolium salt using Na 2 CO 3 catalyzes the intramolecular Stetter reaction, which was followed by air oxidation to reinstall the C-C double bond.

Item Type:	Journal Article
Publication:	Journal of Organic Chemistry
Publisher:	American Chemical Society
Additional Information:	The copyright for this article belongs to American Chemical Society.
Keywords:	Catalysis; Ketones; Sodium Carbonate; Sodium compounds; Transition metals, Air oxidation; C-C double bonds; Carbenes; Cross dehydrogenative couplings; N-heterocyclic carbenes; Naphthoquinones; Stetter reaction, Synthesis (chemical), 1,4 naphthoquinone derivative; benzaldehyde derivative; bicarbonate; carbene; transition element, catalysis; chemical reaction; covalent bond; cross coupling reaction; dehydrogenation; dimerization; oxidation; Review; Stetter reaction; synthesis
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	28 Nov 2022 09:41
Last Modified:	28 Nov 2022 09:41
URI:	https://eprints.iisc.ac.in/id/eprint/78086

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