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Article
Iron Porphyrin-Catalyzed Olefination of Carbonyl Compounds with Ethyl Diazoacetate
Organometallics
  • Guilong Cheng, Iowa State University
  • Gholam A. Mirafzal, Iowa State University
  • L. Keith Woo, Iowa State University
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
3-1-2003
DOI
10.1021/om020904o
Abstract
Iron(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.
Comments

Reprinted (adapted) with permission from Organometallics 22 (2003): 1468, doi:10.1021/om020904o. Copyright 2003 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Guilong 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/