Palladium(0)-catalyzed allylation of highly acidic and non-nucleophilic arenesulfonamides, sulfamide, and cyanamide. II. Formation of medium and large heterocycles

Sílvia Cerezo, Jordi Cortés, Juan Manuel López-Romero, Marcial Moreno-Mañas, Teodor Parella, Roser Pleixats, Anna Roglans

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37 Citations (Scopus)

Abstract

Arenesulfonamides 10, cyanamide 29, and sulfamide 32 react with allylic bis-carbonates 8 (Z and E) and 9 under Pd(0)-catalysis to afford medium and large unsaturated heterocycles instead of three and/or five-membered ring compounds. Stable 15-membered palladium-containing rings were also isolated from arenesulfonamides and 8, with three trans olefinic systems coordinated to the metal. NMR and MALDI-TOF MS experiments were used for structure elucidations. Suitable hydrogenation conditions to give the saturated macrocycles have been found.
Original languageEnglish
Pages (from-to)14885-14904
JournalTetrahedron
Volume54
Issue number49
DOIs
Publication statusPublished - 3 Dec 1998

Keywords

  • Acidic N-nucleophiles
  • Allylation
  • Macrocycles
  • Palladium Catalysis

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