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Intramolecular Arylation of Tertiary Enamides through Pd(OAc)2-Catalyzed Dehydrogenative Cross-Coupling Reaction: Construction of Fused N-Heterocyclic Scaffolds and Synthesis of Isoindolobenzazepine Alkaloids.
Journal article

Intramolecular Arylation of Tertiary Enamides through Pd(OAc)2-Catalyzed Dehydrogenative Cross-Coupling Reaction: Construction of Fused N-Heterocyclic Scaffolds and Synthesis of Isoindolobenzazepine Alkaloids.

  • Zhu W State Key Laboratory of Separation Membranes and Membrane Processes , School of Chemistry and Chemical Engineering Tianjin Polytechnic University , Tianjin 300387 , China.
  • Tong S MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry , Tsinghua University , Beijing 100084 , China.
  • Zhu J Institute of Chemical Sciences and Engineering , Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN , BCH 5304 , 1015 Lausanne , Switzerland.
  • Wang MX MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry , Tsinghua University , Beijing 100084 , China.
  • 2019-02-09
Published in:
  • The Journal of organic chemistry. - 2019
Organic Chemistry
English Pd(OAc)2-catalyzed intramolecular dehydrogenative cross-coupling reaction between tertiary enamides, which were derived from the condensation of 2-arylethylamines and methyl o-acetylbenzoate, and arenes enabled synthesis of 7,8-dihydro-5 H-benzo[4,5]azepino[2,1- a]isoindol-5-one derivatives under mild conditions. The synthetic method was applied in the total synthesis of aporhoeadane alkaloids palmanine, lennoxamine, and chilenamine in only three or four steps.
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  • English
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https://folia.unifr.ch/global/documents/231384
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