Synthesis of aza-heterocycles from oximes by amino-Heck reaction.
Oxidative addition of oximes to palladium(0) complexes generates alkylideneaminopalladium(II) species, which are utilized as key intermediates for carbon-nitrogen bond formation. Various aza-heterocycles, such as pyrrole, pyridine, isoquinoline, spiroimine, and azaazulene, can be synthesized from O-pentafluorobenzoyloximes having an olefinic moiety via an intramolecular Heck-type reaction (amino-Heck reaction) by treatment with a catalytic amount of a Pd(0) complex.
Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Mitsuru
M
Kitamura
Koichi
K
Narasaka
D001372:Aza Compounds / Q000138:chemical synthesis*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D010091:Oximes / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry
D001372:Aza Compounds; D006571:Heterocyclic Compounds; D010091:Oximes; D010165:Palladium