Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol.
[reaction: see text] An SN2 mechanism for the copper-catalyzed amination of diorganozinc reagents by O-benzoyl-N,N-dialkylhydroxylamines is supported by following stereochemically defined organometallics through the reaction and by employing the endocyclic restriction test. A copper-catalyzed electrophilic amination of organomagnesium compounds is also described in which the use of zinc halides has been eliminated.
Campbell
Matthew J
MJ
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Johnson
Jeffrey S
JS
D000586:Amination; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D004583:Electrons; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry; D015032:Zinc / Q000737:chemistry*
D001965:Bromides; D010880:Piperidines; C032727:piperidine; D003300:Copper; D015032:Zinc