Efficient and Sustainable One-pot Synthesis of alpha-Carbonyl Homoallylic Alcohols from Benzaldehyde and Allylic Alcohols Using both NHC and Nickel Catalysts - Université de Lille Accéder directement au contenu
Article Dans Une Revue ChemCatChem Année : 2023

Efficient and Sustainable One-pot Synthesis of alpha-Carbonyl Homoallylic Alcohols from Benzaldehyde and Allylic Alcohols Using both NHC and Nickel Catalysts

Résumé

α-carbonyl homoallylic alcohols have been synthesized in a one-pot reaction from benzaldehyde and allylic alcohols. The nickel-catalyzed allylation of α-hydroxyketones has first been studied and allowed the identification of Ni(cod)2/dppf as the most suitable catalytic system. The tandem reaction that combines the benzoin condensation of aldehydes (synthesis of α-hydroxyketones) promoted by the 1,3-dimethylimidazolium chloride/DBU system and the nickel-catalyzed allylic alkylation with allylic alcohol has been realized in EtOH as green solvent. The reaction is 100 % atom-economical and water is formed as sole by-product. A broad scope of different benzaldehyde derivatives as well as various allylic alcohols is also described.

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Catalyse
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hal-04144631 , version 1 (28-06-2023)

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Yasmina Homrani, Bouchaib Mouhsine, Aurelien Bethegnies, Mohamed Amin El Amrani, Abdallah Karim, et al.. Efficient and Sustainable One-pot Synthesis of alpha-Carbonyl Homoallylic Alcohols from Benzaldehyde and Allylic Alcohols Using both NHC and Nickel Catalysts. ChemCatChem, 2023, 15 (10), pp.e202300038. ⟨10.1002/cctc.202300038⟩. ⟨hal-04144631⟩
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