title: Catalytic formation of ketones from unactivated esters through rhodium chelation-assisted C-O bond activation.
abstract: A new method for building aryl aryl ketones containing heterocyclic rings through chelation-assisted C-O bond activation catalyzed by a rhodium complex has been developed. In this reaction, methyl quinoline-8-carboxylate, methyl quinoxaline-5-carboxylate, and their derivatives were reacted with an excess amount of a substituted phenyl boronic acid in the presence of a rhodium(I) complex to give substituted phenyl(quinolin-8-yl)methanone, phenylquinoxalin-5-ylmethanone, and their derivatives in medium to high yields. The current method offers a highly favorable synthetic pathway to efficiently build related drugs with an 8-benzoylquinoline core structure. This method may prove especially valuable for medicinal chemists for the late-stage introduction of versatile ketone moieties into complex scaffolds for diversity-oriented synthetic strategies.
authors.affiliation: Department of Chemistry, Tianjin University, Tianjin 300072, P. R. of China.
authors.forename: Jingjing
authors.initials: J
authors.lastname: Wang
authors.forename: Sujing
authors.initials: S
authors.lastname: Zuo
authors.forename: Weiqiang
authors.initials: W
authors.lastname: Chen
authors.forename: Xinrui
authors.initials: X
authors.lastname: Zhang
authors.forename: Kaixin
authors.initials: K
authors.lastname: Tan
authors.forename: Yun
authors.initials: Y
authors.lastname: Tian
authors.forename: Jianhui
authors.initials: J
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D002614:Chelating Agents / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*
chemical_list: D002614:Chelating Agents; D004952:Esters; D007659:Ketones; D009942:Organometallic Compounds; D012238:Rhodium