title: Rhodium(III)-Catalyzed Tandem [2+2+2] Annulation-Lactamization of Anilides with Two Alkynoates via Cleavage of Two Adjacent C-H or C-H/C-O bonds.
abstract: An electron-deficient Cp(E) rhodium(III) complex bearing a cyclopentadienyl ligand with two ethyl ester substituents catalyzes the tandem [2+2+2] annulation-lactamization of acetanilides with two alkynoates via cleavage of adjacent two C-H bonds to give densely substituted benzo[cd]indolones. The reactions of meta-methoxy-substituted acetanilides with two alkynoates also provided benzo[cd]indolones via cleavage of adjacent C-H/C-O bonds. Furthermore, 3,5-dimethoxyacetanilides reacted with two alkynoates to give dearomatized spiro compounds.
authors.affiliation: Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.|Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588, Japan.
authors.forename: Miho
authors.initials: M
authors.lastname: Fukui
authors.affiliation: Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan. yshibata@apc.titech.ac.jp.
authors.forename: Yu
authors.initials: Y
authors.lastname: Shibata
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588, Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Hoshino
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
authors.forename: Haruki
authors.initials: H
authors.lastname: Sugiyama
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
authors.forename: Kota
authors.initials: K
authors.lastname: Teraoka
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
authors.forename: Hidehiro
authors.initials: H
authors.lastname: Uekusa
authors.affiliation: Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588, Japan.
authors.forename: Keiichi
authors.initials: K
authors.lastname: Noguchi
authors.affiliation: Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan. ktanaka@apc.titech.ac.jp.|Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588, Japan. ktanaka@apc.titech.ac.jp.
authors.forename: Ken
authors.initials: K
authors.lastname: Tanaka
keywords: alkynes; anilides; annulation; benzo[cd]indolones; rhodium