title: Phosphine-free Suzuki-Miyaura cross-coupling in aqueous media enables access to 2-C-aryl-glycosides.
abstract: A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-α-glycosides and 1,5-anhydro-2-C-aryl-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki-Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with complete regioselectivity at C-2 and enables access to 2-aryl-glycals with different configurations in excellent yields.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, UK.
authors.forename: Isidro
authors.initials: I
authors.lastname: Cobo
authors.forename: M Isabel
authors.initials: MI
authors.lastname: Matheu
authors.forename: Sergio
authors.initials: S
authors.lastname: Castillón
authors.forename: Omar
authors.initials: O
authors.lastname: Boutureira
authors.forename: Benjamin G
authors.initials: BG
authors.lastname: Davis
mesh_terms: D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010720:Phosphines; D014867:Water
chemical_list: D006027:Glycosides; D010720:Phosphines; D014867:Water; C044646:phosphine