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Title: Phenyl-Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide
Authors: Shiue, Jiann-Shyng;Lin, Mei-Huey;Fang, Jim-Min
Contributors: 化學系
Date: 1997-07
Issue Date: 2013-06-06T02:33:18Z
Publisher: American Chemical Society
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.
Relation: The Journal of Organic Chemistry, 62(14): 4643-4649
Appears in Collections:[Department of Chemistry] Periodical Articles

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