Nickel-NHC-catalyzed alpha-arylation of acyclic ketones and amination of haloarenes and unexpected preferential N-arylation of 4-aminopropiophenone.
Arylation of both acyclic ketones and primary and secondary amines was achieved using a new, simple, stable, and easy-to-access nickel(II)-halide complex bearing mixed PPh3/N-heterocyclic carbene ligands as a catalyst precursor. Acyclic ketones were first arylated at the alpha-position with the nickel catalyst. On the other hand, less basic amines, such as diphenylamine and 4-aminobenzophenone, were more favorable in the catalytic amination of haloarenes than basic amines, contrary to previous reports. N-Arylation of 4-aminopropiophenone was found to proceed selectively without causing alpha-arylation of the ketone group.
Matsubara
Kouki
K
Department of Chemistry, Faculty of Science, and School of Medicine, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan. kmatsuba@fukuoka-u.ac.jp
Ueno
Keita
K
Koga
Yuji
Y
Hara
Kenji
K
D000586:Amination; D002384:Catalysis; D006219:Halogens / Q000737:chemistry*; D006844:Hydrocarbons, Cyclic / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*
D006219:Halogens; D006844:Hydrocarbons, Cyclic; D007659:Ketones; D009532:Nickel