title: Expeditious and Solvent-Free Nickel-Catalyzed C-H Arylation of Arenes and Indoles.
abstract: An efficient solvent-free nickel-catalyzed method for C-H bond arylation of arenes and indoles has been developed, which proceeds expeditiously through chelation assistance. The reaction is highly selective for mono-arylation and tolerates sensitive and structurally diverse functionalities, such as halides, ethers, amines, indole, pyrrole and carbazole. This reaction represents the first example of a nickel-catalyzed C-H arylation by monochelate assistance and symbolizes a rare precedent in solvent-free C-H arylation. Mechanistic investigations by various controlled reactions, kinetic studies, and deuterium labeling experiments suggest that the arylation follows a single electron transfer (SET) pathway involving the turnover-limiting C-H nickelation process.
authors.affiliation: Organometallic Synthesis and Catalysis Group, Chemical Engineering, Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune, 411 008, Maharashtra, India), Home page.
authors.forename: Rahul A
authors.initials: RA
authors.lastname: Jagtap
authors.affiliation: Organometallic Synthesis and Catalysis Group, Chemical Engineering, Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune, 411 008, Maharashtra, India), Home page.
authors.forename: Vineeta
authors.initials: V
authors.lastname: Soni
authors.affiliation: Organometallic Synthesis and Catalysis Group, Chemical Engineering, Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune, 411 008, Maharashtra, India), Home page.
authors.forename: Benudhar
authors.identifier: 0000-0002-9257-5236
authors.initials: B
authors.lastname: Punji
mesh_terms: D002384:Catalysis; D006838:Hydrocarbons / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*
chemical_list: D006838:Hydrocarbons; D007211:Indoles; D012997:Solvents; D009532:Nickel
keywords: C−H activation; arylation; heterocycles; homogeneous catalysis; nickel