3 years ago

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

Metal-Free, Brønsted Acid-Catalyzed Formal [3+2] Annulation of Quinone Monoacetals with 2-Naphthols
Trinadh Kaicharla, Anu Jacob, Akkattu T. Biju, Tony Roy
An operationally simple and metal-free cross-coupling of quinone monoacetals (QMAs) with 2-naphthols catalyzed by triflic acid is reported. This formal [3+2] annulation allowed the synthesis of diverse naphtho[2,1-b]benzofuran derivatives in moderate to good yields. Preliminary mechanistic studies reveal the initial nucleophilic substitution of QMAs with 2-naphthols in preference to the mixed acetal formation and subsequent [3,3] sigmatropic rearrangement.

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

DOI: 10.1021/acs.joc.7b02033

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