title: Triorganoindium reagents in selective palladium-catalyzed cross-coupling with iodoimidazoles: synthesis of neurodazine.
abstract: Triorganoindium reagents (R3In, R = aryl, heteroaryl, alkynyl) react selectively under palladium catalysis with N-benzyl-2,4,5-triiodoimidazole to afford the C-2 monocoupling products. The reaction proceeds efficiently for a variety of aryl- and heteroarylindium reagents with the transfer of all three organic groups attached to the metal. The coupling products can be used in a subsequent two-fold cross-coupling to give trisubstituted imidazoles in good yields. This approach was employed to synthesize neurodazine and analogues in good yields.
authors.affiliation: Departamento de Química Fundamental and Centro de Investigaciones Científicas Avanzadas (CICA), Universidade da Coruña , E-15071 A Coruña, Spain.
authors.forename: Cristina
authors.initials: C
authors.lastname: Pérez-Caaveiro
authors.forename: José
authors.initials: J
authors.lastname: Pérez Sestelo
authors.forename: M Montserrat
authors.initials: MM
authors.lastname: Martínez
authors.forename: Luis A
authors.initials: LA
authors.lastname: Sarandeses
mesh_terms: D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
chemical_list: C000597340:1-benzyl-2-(5-(3-chlorophenyl)furan-2-yl)-4,5-bis(4-methoxyphenyl)-1H-imidazole; D001593:Benzyl Compounds; D056831:Coordination Complexes; D007093:Imidazoles; D007202:Indicators and Reagents; C000597338:N-benzyl-2,4,5-triiodoimidazole; D007204:Indium; D010165:Palladium