Palladium(0)-catalyzed allylation of highly acidic and non-nucleophilic arenesulfonamides, sulfamide, and cyanamide. I.

Sílvia Cerezo, Jordi Cortés, Marcial Moreno-Mañas, Roser Pleixats, Anna Roglans

Research output: Contribution to journalArticleResearchpeer-review

53 Citations (Scopus)

Abstract

Arenesulfonamides, sulfamide, and cyanamide are efficiently allylated using allylic carbonates under Pd(0)-catalysis. N-Arenesulfonyl-2,5- dihydropyrroles are obtained by ruthenium-mediated ring closing metathesis of the corresponding N-diallylated compounds. A stereochemical study of the reactions of ethyl cis-(5-methyl-2-cyclohexenyl) carbonate with 2,4,6- triisopropylphenylsulfonamide was performed, clean overall retention of configuration being found with bidentate phosphines.
Original languageEnglish
Pages (from-to)14869-14884
JournalTetrahedron
Volume54
Issue number49
DOIs
Publication statusPublished - 3 Dec 1998

Keywords

  • Allylation
  • Catalysis
  • Palladium
  • Stereochemistry

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