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Metal-Free, Bronsted Acid-Catalyzed Formal 3+2] Annulation of Quinone Monoacetals with 2-Naphthols

Jacob, Anu and Roy, Tony and Kaicharla, Trinadh and Biju, Akkattu T (2017) Metal-Free, Bronsted Acid-Catalyzed Formal 3+2] Annulation of Quinone Monoacetals with 2-Naphthols. In: JOURNAL OF ORGANIC CHEMISTRY, 82 (20). pp. 11269-11274.

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Official URL: http://doi.org/10.1021/acs.joc.7b02033

Abstract

An operationally simple and metal-free crosscoupling of quinone monoacetals (QMAs) with 2-naphthols catalyzed by triflic acid is reported, This formal 3+2] annulation allowed the synthesis of diverse naphtho2,1b]benzofuran derivatives in moderate to good yields. Preliminary mechanistic studies reveal the initial nucleophilic substitution of QMAs with 2-naphthols in preference to die mixed acetal formation and subsequent. 3,3] sigmatropic rearrangement.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 17 Nov 2017 05:10
Last Modified: 17 Nov 2017 05:10
URI: http://eprints.iisc.ac.in/id/eprint/58271

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