Monoligated Pd(0)-catalyzed intramolecular ortho- and para-arylation of phenols for the synthesis of aporphine alkaloids. Synthesis of (−)-lirinine

An intramolecular palladium(0)-mediated ortho-arylation of phenols applied to the synthesis of various substituted aporphines is reported. Most significantly, the efficiency of the transformation was enhanced by the use of monoligated Pd(0) complexes. This methodology was extended to para-arylation...

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Bibliographic Details
Published inTetrahedron Vol. 68; no. 6; pp. 1674 - 1681
Main Authors Hellal, Malik, Singh, Shambhavi, Cuny, Gregory D.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 11.02.2012
Elsevier
Subjects
Alkaloids
Aporphines
Catalysis
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Methodology
Noncondensed benzenic compounds
Organic chemistry
Palladium
Phenol
Phenols
Physical Sciences
Preparations and properties
Science & Technology
Synthesis (chemistry)
Tetrahedrons
Transformations
Alkaloids
Phenol
Palladium
Catalysis
Aporphines
NAPHTHOLS
PICTET-SPENGLER
SRN1
ARYL HALIDES
DERIVATIVES
CYCLIZATION
Intramolecular reaction
Arylation
Catalytic reaction
Nitrogen heterocycle
Palladium complex
Transition metal
Alkaloid
Phenols
Chemical synthesis
Platinoid
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Summary:An intramolecular palladium(0)-mediated ortho-arylation of phenols applied to the synthesis of various substituted aporphines is reported. Most significantly, the efficiency of the transformation was enhanced by the use of monoligated Pd(0) complexes. This methodology was extended to para-arylation of phenols and employed in the synthesis of the aporphine alkaloid (−)-lirinine. [Display omitted]
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.12.022