[Development of environmentally friendly organometallic catalysis for drug discovery and its application to heterocyclic chemistry].
Two new catalysts, ruthenium hydride with a nitrogen-containing heterocyclic carbene (A) and an organopalladium catalyst supported on a sulfur-terminated semi-conductor, gallium arsenide (001) (B) were discovered. Both catalysts are environmentally benign, because A can yield indole derivatives with good atom economy, and B can catalyze the Mizoroki-Heck reaction more than 10 times with only trace amounts of leached palladium (ppb level). Substituted 1,2-dihydroquinoline, indole and 3-methylene-2,3-dihydroindole were also prepared selectively from the common starting material, N-allyl-o-vinylaniline, and catalyst by slight modification of the reaction conditions. These procedures address an important issue in diversity-oriented synthesis. These methods utility were demonstrated by application to biologically active natural products synthesis.
Arisawa
Mitsuhiro
M
Graduate School of Pharmaceutical Sciences, Hokkaido University, Kata-12, Nishi-6, Sapporo, Japan. arisawa@pharm.hokudai.ac.jp
D000475:Alkenes; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic; D015195:Drug Design; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis; D055601:Organic Chemistry Phenomena; D009942:Organometallic Compounds; D010165:Palladium; D012428:Ruthenium