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

Ghosh, Arghya ; Patra, Atanu ; Mukherjee, Subrata ; Biju, Akkattu T. (2019) Synthesis of 2-Aryl Naphthoquinones by the Cross-Dehydrogenative Coupling Involving an NHC-Catalyzed endo-Stetter Reaction The Journal of Organic Chemistry, 84 (2). pp. 1103-1110. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/acs.joc.8b02931

Related URL: http://dx.doi.org/10.1021/acs.joc.8b02931

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 Na2CO3 catalyzes the intramolecular Stetter reaction, which was followed by air oxidation to reinstall the C-C double bond.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:128611
Deposited On:03 Nov 2022 06:44
Last Modified:03 Nov 2022 06:44

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