Brønsted Acid Catalyzed Functionalization of Aromatic Alcohols through Nucleophilic Substitution of Hydroxyl Group

The Journal of Organic Chemistry
Abhishek Kumar Mishra, Srijit Biswas

Abstract

The hydroxyl groups of naphthol and tautomerizable phenol derivatives have been substituted by O-, S-, N-, and C-centered nucleophiles under solvent-free reaction conditions. The products are generated in good to excellent yields. para-Toluenesulfonic acid exhibits the best catalytic activity compared to other Brønsted acids. Experimental observations suggest that the reaction proceeds through the intermediacy of the keto tautomer of naphthol. Nucleophilic addition to the carbonyl group followed by elimination of water generates the desired product. The present methodology provides access to substituted naphtho[2,1-b]furan derivatives. The products generated using N-centered nucleophiles can be further transformed to important classes of organic molecules such as benzocarbazole and imidazole derivatives.

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Citations

Feb 7, 2017·The Journal of Organic Chemistry·Jin HuangRui-Xiang Li
Jun 20, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bingqiao WangQiang Tang
Nov 8, 2019·Chemical Communications : Chem Comm·Saori TaniiMasahiko Yamaguchi
May 1, 2019·The Journal of Organic Chemistry·Zicong ChenChau Ming So

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