The Journal of Organic Chemistry

Phenyl-Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide

JS Shiue, MH Lin, JM Fang

Index: Shiue, Jiann-Shyng; Lin, Mei-Huey; Fang, Jim-Min Journal of Organic Chemistry, 1997 , vol. 62, # 14 p. 4643 - 4649

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Citation Number: 55

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- ...