Jacob, Anu ; Roy, Tony ; Kaicharla, Trinadh ; Biju, Akkattu T. (2017) Metal-Free, Brønsted Acid-Catalyzed Formal [3+2] Annulation of Quinone Monoacetals with 2-Naphthols The Journal of Organic Chemistry, 82 (20). pp. 11269-11274. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/acs.joc.7b02033
Related URL: http://dx.doi.org/10.1021/acs.joc.7b02033
Abstract
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]benzofuranderivatives 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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 128635 |
| Deposited On: | 03 Nov 2022 06:50 |
| Last Modified: | 03 Nov 2022 06:50 |
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