Iron Porphyrin-Catalyzed Olefination of Carbonyl Compounds with Ethyl Diazoacetate

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2003-03-01
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Cheng, Guilong
Mirafzal, Gholam
Woo, L.
Woo, L. Keith
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Woo, L.
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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.

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<p>Reprinted (adapted) with permission from <em>Organometallics</em> 22 (2003): 1468, doi:<a href="http://dx.doi.org/10.1021/om020904o" target="_blank">10.1021/om020904o</a>. Copyright 2003 American Chemical Society.</p>
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