Phosphoric-Acid-Catalyzed ortho -Selective Intramolecular Cyclodehydration Reaction of Phenols and Anilines

Organic Letters 2026

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Authors: Sukit Chonradeenitchakul, Takahito Kuribara, Honoka Yuba, Tetsuhiro Nemoto
DOI: 10.1021/acs.orglett.5c05043
Cited by: 0
References: 49

Abstract

-selective intramolecular cyclodehydration of phenols and anilines. In the presence of 1 mol % of a phosphoric acid catalyst, resorcinol, 3-aminophenol, and 1,3-phenylenediamine derivatives underwent highly regioselective cyclodehydration to afford 4-hydroxybenzofuran, 4-hydroxyindole, 4-aminobenzofuran, and 4-aminoindole derivatives in up to 97% yield and >99:1 regioselectivity. The resulting products were further derivatized and applied in a formal synthesis of tambromycin. Kinetic studies and DFT calculations elucidated the regioselective reaction mechanism.

Fields of Study & Subjects

Asymmetric Synthesis and Catalysis Synthesis and Biological Activity Catalytic C–H Functionalization Methods

Publication details

Journal / source
Organic Letters
Volume
28
Issue
2
Pages
837–842
Publication date
1 January 2026
Language
EN