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American Chemical Society, Organic Letters, 19(17), p. 4846-4849, 2015

DOI: 10.1021/acs.orglett.5b02413

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Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers

Journal article published in 2015 by Alexander S. Henderson, Sandra Medina, John F. Bower, M. Carmen Galan ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

A general and practical route to carbohydrate-aryl ethers by nucleophilic aromatic substitution (SNAr) is reported. Upon treatment with KHMDS, C-O bond formation occurs between carbohydrate alcohols and a diverse range of fluorinated (hetero)aromatics to provide the targets in good to excellent yields. Commercially available arylating agents, high atom economy, and high regioselectivity are notable features of the protocol. The aryl ether products have potential for wide-ranging applications as exemplified by the synthesis of a novel chiral P,N-ligand.