Comparative study of TmI2, SmI2, and SmI2/HMPA in the cross-coupling reactions of 2-acetylthiophene and thiophene-2-carboxylate with carbonyl compounds |
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| Authors: | Jiun-Jie Shie William J Evans Jim-Min Fang |
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| Affiliation: | a Department of Chemistry, National Taiwan University, Taipei 106, Taiwan
b Department of Chemistry, University of California Irvine, CA 92697-2025, USA |
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| Abstract: | The cross-coupling reactions of acetylthiophene or ethyl thiophene-2-carboxylate with aldehydes or ketones were achieved in a regioselective manner by using thulium diiodide in THF solution. Similar coupling reactions were also realized by using samarium diiodide together with excess amounts of hexamethylphosphoramide (HMPA). However, ethyl thiophene-2-carboxylate was inert in SmI2/THF solution, and acetylthiophene was simply reduced to thienylethanol by SmI2 in the absence of HMPA. |
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| Keywords: | Thulium diiodide Samarium diiodide Hexamethylphosphoramide Coupling reaction |
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