Catalytic Allylic Chlorination of Natural Terpenic Olefins Using Supported and Nonsupported Lewis Acid Catalysts

A mild and convenient method for the allylic chlorination of naturally occurring terpenic olefins was investigated in the presence of different supported and non-supported Lewis acid catalysts. The reaction has been tested on carvone as a model substrate in the presence of sodium hypochlorite as chl...

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Bibliographic Details
Published in:Journal of chemistry 2020-10, Vol.2020 (2020), p.1-8
Main Authors: El Firdoussi, Larbi, Orfi, Hamza, Laayati, Mouhsine, Mekkaoui, Ayoub Abdelkader, El Houssame, Soufiane
Format: Article
Language:English
Subjects:
Alkenes
Catalysts
Chloride
Chlorination
Chlorine
Ferric chloride
Iron chlorides
Lewis acid
Natural products
Olefins
Reaction time
Selectivity
Sodium
Sodium hypochlorite
Stoichiometry
Substrates
Transition metal compounds
Transition metals
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Summary:A mild and convenient method for the allylic chlorination of naturally occurring terpenic olefins was investigated in the presence of different supported and non-supported Lewis acid catalysts. The reaction has been tested on carvone as a model substrate in the presence of sodium hypochlorite as chlorine donor. The scope and limitations of transition metal-based Lewis acid catalysts, stoichiometry, and substrate structure were evaluated. Among the iron precursors used, FeCl3 and FeCl2 provide the promise of a general approach to allylic or vinylic chlorination reaction. Various terpenic olefins were examined in the presence of FeCl3/NaOCl combination system. The catalytic chlorination proceeds under mild conditions with short reaction time and shows a high selectivity affording the corresponding chlorides in good to excellent yields.
ISSN:2090-9063
2090-9071
DOI:10.1155/2020/2563634