Scope of aminomethylations via Suzuki-Miyaura cross-coupling of organotrifluoroborates.
We previously reported the Suzuki-Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to excellent yields to give N,N-dialkylbenzylic amines. The aminomethylation of alkenyl bromides was also examined.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Gormisky
Paul E
PE
Sandrock
Deidre L
DL
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D002722:Chlorobenzenes; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D008745:Methylation; D010165:Palladium
D000588:Amines; D001555:Benzene Derivatives; D001881:Borates; D002722:Chlorobenzenes; D006846:Hydrocarbons, Halogenated; D010165:Palladium