title: Metal-free coupling of saturated heterocyclic sulfonylhydrazones with boronic acids.
abstract: The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic boronic acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp(2)-sp(3) linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.
authors.affiliation: Department of Chemistry, University of Cambridge , Cambridge, CB2 1EW, U.K.
authors.forename: Daniel M
authors.initials: DM
authors.lastname: Allwood
authors.forename: David C
authors.initials: DC
authors.lastname: Blakemore
authors.forename: Alan D
authors.initials: AD
authors.lastname: Brown
authors.forename: Steven V
authors.initials: SV
authors.lastname: Ley
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D006571:Heterocyclic Compounds; D006835:Hydrazones; D008670:Metals