Skeletal Formation of Carbocycles with CO<sub>2</sub>: Selective Synthesis of Indolo[3,2-<i>b</i>]carbazoles or Cyclophanes from Indoles, CO<sub>2</sub>, and Phenylsilane
Sha Li, S. NAKAHARA, Taishin Adachi, Takumi Murata, Kazuto Takaishi, Tadashi Ema
Abstract
The catalytic reactions of indoles with CO 2 and phenylsilane afforded indolo[3,2- b ]carbazoles, where the fused benzene ring was constructed by forming two C–H bonds and four C–C bonds with two CO 2 molecules via deoxygenative conversions. Nine-membered cyclophanes made up of three indoles and three CO 2 molecules were also obtained, where the cyclophane framework was constructed by forming six C–H bonds and six C–C bonds. These multicomponent cascade reactions giving completely different carbocycles were switched simply by choosing the solvent, acetonitrile or ethyl acetate.
Topics & Concepts
ChemistryPhenylsilaneCatalysisMedicinal chemistryOrganic chemistryComputational chemistryStereochemistryCarbon dioxide utilization in catalysisAsymmetric Hydrogenation and CatalysisCO2 Reduction Techniques and Catalysts