title: Preparation of unsymmetrical ketones from tosylhydrazones and aromatic aldehydes via formyl C-H bond insertion.
abstract: Preparation of ketones by insertion of diazo compounds into the formyl C-H bond of an aldehyde is an attractive procedure, but use of structurally diverse diazo compounds is hampered by preparation and safety issues. A convenient procedure for the synthesis of unsymmetrical ketones from bench-stable tosylhydrazones and aryl aldehydes is reported. The procedure can be performed in one pot from the parent carbonyl compound and needs only a base, with no additional promoters being required.
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: Steven V
authors.initials: SV
authors.lastname: Ley
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D006835:Hydrazones / Q000737:chemistry*; D006860:Hydrogen Bonding; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000447:Aldehydes; D001391:Azo Compounds; D006835:Hydrazones; D007659:Ketones