Palladium-Catalyzed Sequential Alkylation−Alkenylation Reactions. Application to the Synthesis of 2-Substituted-4-Benzoxepines and 2,5-Disubstituted-4-Benzoxepines

The synthesis of 2-substituted-4-benzoxepines and 2,5-disubstituted-4-benzoxepines from aryl iodides and bromoenoates is described. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the reaction conditions (Pd(OAc)2 (10 mol %)...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-05, Vol.67 (11), p.3972-3974
Main Authors: Lautens, Mark, Paquin, Jean-François, Piguel, Sandrine
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:The synthesis of 2-substituted-4-benzoxepines and 2,5-disubstituted-4-benzoxepines from aryl iodides and bromoenoates is described. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the reaction conditions (Pd(OAc)2 (10 mol %), tri-2-furylphosphine (20 mol %), norbornene (2 equiv), Cs2CO3 (2 equiv), CH3CN, 85 °C), moderate to excellent yields of benzoxepines bearing numerous substituents (Me, F, Cl, etc.) are obtained.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo025730z