title: Palladium-catalyzed Kumada coupling reaction of bromoporphyrins with silylmethyl Grignard reagents: preparation of silylmethyl-substituted porphyrins as a multipurpose synthon for fabrication of porphyrin systems.
abstract: We have developed an efficient method for preparing silylmethyl-substituted porphyrins via the palladium-catalyzed Kumada cross-coupling reaction of bromoporphyrins with silylmethyl Grignard reagents. We demonstrated the synthetic utility of these silylmethylporphyrins as a multipurpose synthon for fabricating porphyrin derivatives through a variety of transformations of the silylmethyl groups, including the DDQ-promoted oxidative conversion to CHO, CH(2)OH, CH(2)OMe, and CH(2)F functionalities and the fluoride ion-mediated desilylative introduction of carbon-carbon single and double bonds.
authors.affiliation: Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan.
authors.forename: Noriaki
authors.initials: N
authors.lastname: Sugita
authors.forename: Satoshi
authors.initials: S
authors.lastname: Hayashi
authors.forename: Fumio
authors.initials: F
authors.lastname: Hino
authors.forename: Toshikatsu
authors.initials: T
authors.lastname: Takanami
mesh_terms: D002384:Catalysis; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011166:Porphyrins / Q000737:chemistry*
chemical_list: D007202:Indicators and Reagents; D017646:Organosilicon Compounds; D011166:Porphyrins; D010165:Palladium