title: Pd(II)-catalyzed ligand controlled synthesis of methyl 1-benzyl-1H-indole-3-carboxylates and bis(1-benzyl-1H-indol-3-yl)methanones.
abstract: A simple change of ligand and solvent allows controlled, effective switching between cyclization-carbonylation and cyclization-carbonylation-cyclization-coupling (CCC-coupling) reactions of 2-alkynylanilines catalyzed by palladium(II). The use of a [Pd(tfa)2(box)] catalyst in iPrOH afforded symmetrical ketones bearing two indoles in good yields; replacing the catalyst and solvent with Pd(tfa)2 and DMSO-MeOH led to the formation of methyl 1-benzyl-1H-indole-3-carboxylates in good yields.
authors.affiliation: Toho University, Funabashi, Japan. kkk@phar.toho-u.ac.jp.
authors.forename: Rong
authors.initials: R
authors.lastname: Shen
authors.forename: Taichi
authors.initials: T
authors.lastname: Kusakabe
authors.forename: Keisuke
authors.initials: K
authors.lastname: Takahashi
authors.forename: Keisuke
authors.initials: K
authors.lastname: Kato
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008024:Ligands; D010165:Palladium / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D007211:Indoles; D007659:Ketones; D008024:Ligands; D010165:Palladium