173276-66-9

Upstream product

• 498-62-4 3-thiophene carboxaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 80423-71-8 2-(4-methoxy-benzoyl)-thiophene-3-carbaldehyde 
• 220338-01-2 3-((Z)-2-Benzylsulfanyl-vinyl)-5-(4-methoxy-phenyl)-2,5-dihydro-furan-2-ol 

Relevant academic research and scientific papers

Coupling reactions and coupling-alkylations of thiophenecarbaldehydes promoted by samarium diiodide

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.

Samarium diiodide promoted coupling of thiophenecarbaldehydes

Thiophene-2-carbaldehyde adds to aromatic and aliphatic aldehydes with the mediation of samarium diiodide and hexamethylphosphoramide.These hydroxyalkylations occur at the 5-position of thiophene-2-carbaldehyde.The self- and cross-coupling reactions of thiophene-3-carbaldehyde occur at the 2-position.S-Alkylation of the reaction intermediates gives substituted γ-lactols.