title: Enantioselective palladium-catalyzed C-H functionalization of indoles using an axially chiral 2,2'-bipyridine ligand.
abstract: A palladium-catalyzed enantioselective CH functionalization of indoles was achieved with an axially chiral 2,2'-bipyridine ligand, thus providing the desired indol-3-acetate derivatives with up to 98 % ee. Moreover, the reaction protocol was also effective for asymmetric OH insertion reaction of phenols using α-aryl-α-diazoacetates. This represents the first successful application of bipyridine ligands with axial chirality in palladium-catalyzed carbene migratory insertion reactions.
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P.R. China).
authors.forename: Xiang
authors.initials: X
authors.lastname: Gao
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P.R. China).
authors.forename: Bo
authors.initials: B
authors.lastname: Wu
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P.R. China).
authors.forename: Wen-Xue
authors.initials: WX
authors.lastname: Huang
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P.R. China).
authors.forename: Mu-Wang
authors.initials: MW
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P.R. China). ygzhou@dicp.ac.cn.|Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin 300071 (P.R. China). ygzhou@dicp.ac.cn.
authors.forename: Yong-Gui
authors.initials: YG
authors.lastname: Zhou
mesh_terms: D015082:2,2'-Dipyridyl / Q000737:chemistry*; D000085:Acetates / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D007211:Indoles; D008024:Ligands; D010636:Phenols; C030011:carbene; D015082:2,2'-Dipyridyl; D010165:Palladium; D008697:Methane
keywords: asymmetric catalysis; chirality; diazo compounds; ligand design; palladium