title: Manganese- and Borane-Mediated Synthesis of Isobenzofuranones from Aromatic Esters and Oxiranes via C-H Bond Activation.
abstract: A manganese- and borane-mediated synthesis of isobenzofuranones from esters and oxiranes is developed. The reaction proceeded at aromatic, heteroaromatic, and olefinic C-H bonds with high functional group tolerance. This is the first example of a manganese-catalyzed C-H transformation using an oxygen-directing group. Triphenylborane played an important role in this reaction to cooperatively promote the annulation reaction. Kinetic isotope effect experiments revealed that C-H bond activation of the aromatic rings was the rate-determining step.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.|CREST, Japan Science and Technology Agency (JST), 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Sueki
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Zijia
authors.initials: Z
authors.lastname: Wang
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.|CREST, Japan Science and Technology Agency (JST), 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Yoichiro
authors.initials: Y
authors.lastname: Kuninobu
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry; D004952:Esters; D008345:Manganese / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001572:Benzofurans; D001880:Boranes; D004852:Epoxy Compounds; D004952:Esters; D008345:Manganese