title: Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.
abstract: A direct C-H functionalization approach to produce aryl(azaaryl)methylamines from azaarylmethylamines without directing groups is described. Under conditions where the azaarylmethylamines' C-H is reversibly deprotonated, a Pd(OAc)(2)/NIXANTPHOS-based catalyst couples the resulting carbanions with various aryl halides to provide aryl(azaaryl)methylamines. This umpolung strategy directly provides tertiary amines without protecting or activating groups.
authors.affiliation: Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Byeong-Seon
authors.initials: BS
authors.lastname: Kim
authors.affiliation: Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.|Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Puebla 72570, Mexico.
authors.forename: Jacqueline
authors.initials: J
authors.lastname: Jiménez
authors.affiliation: Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.|Department of Medicinal Plants, Agronomy College, Sichuan Agricultural University, 211 Huimin Roadd, Wenjiang Region, Chengdu 611130, PR China.
authors.forename: Feng
authors.initials: F
authors.lastname: Gao
authors.affiliation: Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D008744:Methylamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: D001372:Aza Compounds; D008744:Methylamines; D010165:Palladium