title: A versatile approach to Ullmann C-N couplings at room temperature: new families of nucleophiles and electrophiles for photoinduced, copper-catalyzed processes.
abstract: The use of light to facilitate copper-catalyzed cross-couplings of nitrogen nucleophiles can enable C-N bond formation to occur under unusually mild conditions. In this study, we substantially expand the scope of such processes, establishing that this approach is not limited to reactions of carbazoles with iodobenzene and alkyl halides. Specifically, we demonstrate for the first time that other nitrogen nucleophiles (e.g., common pharmacophores such as indoles, benzimidazoles, and imidazoles) as well as other electrophiles (e.g., hindered/deactivated/heterocyclic aryl iodides, an aryl bromide, an activated aryl chloride, alkenyl halides, and an alkynyl bromide) serve as suitable partners. Photoinduced C-N bond formation can be achieved at room temperature using a common procedure with an inexpensive catalyst (CuI) that does not require a ligand coadditive and is tolerant of moisture and a variety of functional groups.
authors: Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
authors: Daniel T
authors: DT
authors: Ziegler
authors: Junwon
authors: J
authors: Choi
authors: José María
authors: JM
authors: Muñoz-Molina
authors: Alex C
authors: AC
authors: Bissember
authors: Jonas C
authors: JC
authors: Peters
authors: Gregory C
authors: GC
authors: Fu
mesh_terms: D002227:Carbazoles / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry; D015394:Molecular Structure; D055668:Photochemical Processes; D013696:Temperature
chemical_list: D002227:Carbazoles; D006846:Hydrocarbons, Halogenated; D007454:Iodides; D007462:Iodobenzenes; D003300:Copper; C073870:cuprous iodide; C031905:iodobenzene