Abstract
By mediation of samarium diiodide and hexamethylphosphoramide, benzaldehydes and acetophenones underwent self- and cross-couplings to give the products having linkages at the para-carbons of phenyl rings and the carbonyl groups. The phenyl-carbonyl coupling of 2,5-dimethoxybenzaldehyde generated a Sm(III)-enolate intermediate, which was trapped by alkyl halides in a stereospecific manner to give uncommon 1,4-dialkyl-2,5-cyclohexadiene-1-carboxaldehydes. The benzaldehydes bearing tethered carbonyl chains proceeded with intramolecular phenyl-carbonyl couplings to afford fused benzocycles.
| Original language | English |
|---|---|
| Pages (from-to) | 4643-4649 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 62 |
| Issue number | 14 |
| DOIs | |
| Publication status | Published - 1997 Jan 1 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry
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Shiue, J. S., Lin, M. H., & Fang, J. M. (1997). Phenyl-Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide. Journal of Organic Chemistry, 62(14), 4643-4649. https://doi.org/10.1021/jo9702498