title: Palladium-Catalyzed Pyrazole-Directed sp3C-H Bond Arylation for the Synthesis of β-Phenethylamines.
abstract: We have developed a method for palladium-catalyzed, pyrazole-directed sp3C-H bond arylation by aryl iodides. The reaction employs a Pd(OAc)2catalyst at 5-10 mol % loading and silver(I) oxide as a halide-removal agent, and it proceeds in acetic acid or acetic acid/hexafluoroisopropanol solvent. Ozonolysis of the pyrazole moiety affords pharmaceutically important β-phenethylamines.
authors.affiliation: Department of Chemistry, University of Houston, Houston, TX, 77204-5003, USA.|Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383, Wrocław, Poland.
authors.forename: Nurbey
authors.initials: N
authors.lastname: Gulia
authors.affiliation: Department of Chemistry, University of Houston, Houston, TX, 77204-5003, USA.
authors.forename: Olafs
authors.identifier: 0000-0003-2642-2992
authors.initials: O
authors.lastname: Daugulis
mesh_terms: D002384:Catalysis; D007454:Iodides / Q000138:chemical synthesis / Q000737:chemistry; D010087:Oxides / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D010627:Phenethylamines / Q000138:chemical synthesis* / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry
chemical_list: D007454:Iodides; D010087:Oxides; D010627:Phenethylamines; D011720:Pyrazoles; D018030:Silver Compounds; C031280:pyrazole; D010165:Palladium; C040225:disilver oxide
keywords: C−C coupling; C−H activation; arenes; homogeneous catalysis; palladium