title: DMSO/I2 mediated C-C bond cleavage of α-ketoaldehydes followed by C-O bond formation: a metal-free approach for one-pot esterification.
abstract: A novel and efficient I2/DMSO mediated metal-free strategy is presented for the direct C-C bond cleavage of aryl-/heteroaryl- or aliphatic α-ketoaldehydes by C2-decarbonylation and C1-carbonyl oxidation to give the corresponding carboxylic acids followed by esterification in one pot, offering excellent yields in both the steps. Here, DMSO acts as the oxygen source/oxidant and this reaction works very well under both conventional heating and microwave irradiation. This is a very simple and convenient protocol.
authors.affiliation: Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu-180 001, India. sdsawant@iiim.res.in sawant.rrl@gmail.com.
authors.forename: Vunnam
authors.initials: V
authors.lastname: Venkateswarlu
authors.forename: K A
authors.initials: KA
authors.lastname: Aravinda Kumar
authors.forename: Sorav
authors.initials: S
authors.lastname: Gupta
authors.forename: Deepika
authors.initials: D
authors.lastname: Singh
authors.forename: Ram A
authors.initials: RA
authors.lastname: Vishwakarma
authors.forename: Sanghapal D
authors.initials: SD
authors.lastname: Sawant
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D019817:Benzoic Acid / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D004951:Esterification; D004952:Esters / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D010084:Oxidation-Reduction; D012997:Solvents
chemical_list: D000447:Aldehydes; D002264:Carboxylic Acids; D004952:Esters; D007659:Ketones; D008670:Metals; D012997:Solvents; D019817:Benzoic Acid; D007455:Iodine; D004121:Dimethyl Sulfoxide