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Synthesis of aryl ethers of carbohydrates via reaction with arynes: selective O-arylation of trans-vicinal dihydroxyl groups in carbohydrates

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Abstract

A new method for the O-arylation of carbohydrates under metal-free conditions using arynes as an aryl source has been developed. This approach works well with mono, di and trihydroxy compounds. Preferential O-arylation takes place at primary over secondary and equatorial over axial. Site-selective O-arylation was achieved with the substrate having trans vicinal diequatorial hydroxyls.

Graphical abstract: Synthesis of aryl ethers of carbohydrates via reaction with arynes: selective O-arylation of trans-vicinal dihydroxyl groups in carbohydrates

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Article information


Submitted
13 Mar 2020
Accepted
14 Apr 2020
First published
16 Apr 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Synthesis of aryl ethers of carbohydrates via reaction with arynes: selective O-arylation of trans-vicinal dihydroxyl groups in carbohydrates

M. Bhardwaj, N. Hussain, I. A. Zargar, A. K. Dash and D. Mukherjee, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00540A

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