Iron Porphyrin-Catalyzed Olefination of Carbonyl Compounds with Ethyl DiazoacetateOrganometallics
Publication VersionPublished Version
AbstractIron(II) meso-tetraphenylporphyrin is an efficient catalyst for the selective olefination of a variety of aromatic and aliphatic aldehydes with use of ethyl diazoacetate in the presence of triphenylphosphine. These reactions gave olefin products in excellent yields (>85%) with high selectivity for the E-isomer (>90%). For the olefination of ketones, the reactions were generally slow and the selectivities were low compared with those observed with aldehydes. Iron(III)meso-tetraphenylporphyrin chloride, reduced in situ, could be used as an olefination precatalyst to produce similar yields and selectivities. The olefination mechanism was investigated and the likely pathways are discussed.
Copyright OwnerAmerican Chemical Society
Citation InformationGuilong Cheng, Gholam A. Mirafzal and L. Keith Woo. "Iron Porphyrin-Catalyzed Olefination of Carbonyl Compounds with Ethyl Diazoacetate" Organometallics Vol. 22 Iss. 7 (2003) p. 1468 - 1474
Available at: http://works.bepress.com/l-woo/86/