Oxidative Coupling of 2-Naphthols and 1-Naphthylamines Using I 2 /O 2 Reagent

The Journal of Organic Chemistry 2026

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Authors: Modala Ramusagar, Eagala Ramesh, Masilamani Shanmugaraja, Mariappan Periasamy
DOI: 10.1021/acs.joc.5c02175
Cited by: 0
References: 46

Abstract

A facile and simple method has been developed for the synthesis of derivatives of 1,1′-bi-2-naphthols (BINOL) and [1,1′-binaphthalene]-4,4′-diamine (naphthidines) by oxidative homocoupling of 2-naphthols and N -substituted-1-naphthylamines using I 2 /O 2 as an oxidant in dichloromethane (DCM) solvent to obtain 63–95% yields. This method works in the presence of I 2 /O 2 as the oxidant and does not require a metal catalyst. The radical cation mechanism was proposed by considering the formation of radical cation intermediates, which were detected by electron paramagnetic resonance spectroscopy.

Fields of Study & Subjects

Axial and Atropisomeric Chirality Synthesis Catalytic C–H Functionalization Methods Catalytic Cross-Coupling Reactions

Publication details

Journal / source
The Journal of Organic Chemistry
Volume
91
Issue
2
Pages
925–932
Publication date
2 January 2026
Language
EN