Phenyl-Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide

Jiann Shyng Shiue, Mei Huey Lin, Jim Min Fang

Research output: Contribution to journalArticle

52 Citations (Scopus)

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 languageEnglish
Pages (from-to)4643-4649
Number of pages7
JournalJournal of Organic Chemistry
Volume62
Issue number14
DOIs
Publication statusPublished - 1997 Jan 1

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Benzaldehydes
Hempa
Bearings (structural)
Acetophenones
Carbon
samarium diiodide

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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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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Phenyl-Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide. / Shiue, Jiann Shyng; Lin, Mei Huey; Fang, Jim Min.

In: Journal of Organic Chemistry, Vol. 62, No. 14, 01.01.1997, p. 4643-4649.

Research output: Contribution to journalArticle

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