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Issue 74, 2016
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A copper catalyzed azidation and peroxidation of β-naphthols via an oxidative dearomatization strategy

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Abstract

Dearomatizative azidation and peroxidation of β-naphthols have been explored using copper bromide as a catalyst. These reactions lead to highly valuable naphthalenone derivatives such as quaternary azide derivatives and quaternary peroxide derivatives in good yields. This method paves an excellent way for synthesizing azides and peroxides which serve as masked surrogates for their corresponding amines and alcohols. Using this method, optically pure binol derivatives were transformed to their corresponding chiral naphthalenones in excellent yields with moderate enantioselectivity.

Graphical abstract: A copper catalyzed azidation and peroxidation of β-naphthols via an oxidative dearomatization strategy

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Supplementary files

Article information


Submitted
11 Jun 2016
Accepted
11 Aug 2016
First published
11 Aug 2016

Chem. Commun., 2016,52, 11084-11087
Article type
Communication

A copper catalyzed azidation and peroxidation of β-naphthols via an oxidative dearomatization strategy

J. Dhineshkumar, P. Samaddar and K. R. Prabhu, Chem. Commun., 2016, 52, 11084 DOI: 10.1039/C6CC04894C

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