Metal-free, brønsted acid-catalyzed formal [3+2] annulation of quinone monoacetals with 2-naphthols
| Title | Metal-free, brønsted acid-catalyzed formal [3+2] annulation of quinone monoacetals with 2-naphthols |
| Publication Type | Journal Article |
| Year of Publication | 2017 |
| Authors | Jacob, A, Roy, T, Kaicharla, T, Biju, AT |
| Journal | Journal of Organic Chemistry |
| Volume | 82 |
| Date Published | SEP |
| Type of Article | Article |
| 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. |
| DOI | 10.1021/acs.joc.7b02033 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 4.785 |
Divison category:
Organic Chemistry