Phenyl?Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide
Resource
Journal of Organic Chemistry 62 (14): 4643-4649
Journal
Journal of Organic Chemistry
Journal Volume
62
Journal Issue
14
Pages
4643-4649
Date Issued
1997
Date
1997
Author(s)
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.
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Type
journal article
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