title: Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers.
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.
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Henderson
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Sandra
authors.initials: S
authors.lastname: Medina
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: John F
authors.initials: JF
authors.lastname: Bower
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Galan