Journal
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
Volume 16, Issue 8, Pages 569-576Publisher
WILEY
DOI: 10.1002/poc.661
Keywords
mechanism; carbonylation; organolithium; heterocycles; radicals; electron transfer
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The reaction of lithium derivatives of aromatic heterocycles with carbon monoxide was studied under several reaction conditions: 2-furyllithium afforded only one product, the tetrahydro-2-furaldehyde (25% yield). On the other hand, 2-thienyllithium and 5-methyl-2-furyllithium gave two and five products, respectively. Although in relatively low yields, formation of highly functionalized. compounds takes place in a fast process under mild conditions. For 1,4-dihydroxy-1,4-bis(5-methyl-2-furanyl) butane-2,3-dione, reaction conditions were achieved to obtain this difficult to prepare derivative in 50% yield. To the best of our knowledge, this is the first report on the reaction of lithiated aromatic heterocycles with CO: evidence is given on the involvement of proton transfers in the reactions of 2-furyllithium and 2-thienyllithium, while the reaction of 5-methyl-2-furyllithium seems to proceed through an electron transfer as the first step. Copyright (C) 2003 John Wiley Sons, Ltd.
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