Coupling Reactions and Coupling?Alkylations of Thiophenecarbaldehydes Promoted by Samarium Diiodide
Resource
Journal of Organic Chemistry 64 (2): 394-399
Journal
Journal of Organic Chemistry
Journal Volume
64
Journal Issue
2
Pages
394-399
Date Issued
1999
Date
1999
Author(s)
Yang, Shyh-Ming
Abstract
The coupling reactions of 2-thiophenecarbaldehyde with aromatic or aliphatic aldehydes were promoted by samarium diiodide in the presence of hexamethylphosphoramide to give C-5 hydroxyalkylation products. The coupling reactions of 3-thiophenecarbaldehyde occurred at C-2, and the subsequent alkylations occurred at the sulfur atom, accompanied by a concurrent opening of the thiophene ring to afford γ-lactols. Double hydroxyalkylations of 2- and 3-thiophenecarbaldehydes were also carried out under appropriate reaction conditions. Synthetic applications of these thiophenecarbonyl coupling products were demonstrated, for example, by elaboration to furans, butenolides, and thiophene-fused polycyclic compounds.
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Type
journal article
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