Alcohol Oxidations by Schiff Base Manganese(III) Complexes

Asymmetric Schiff base manganese(III) complexes involving salen ligands, N,N'‐bis(salicylidene)2,3‐diaminopyridine, N,N'‐bis(3‐methoxysalicylidene)2,3‐diaminopyridine, N,N'‐bis(3,5‐di‐tert‐butylsalicylidene)2,3‐diaminopyridine and N,N'‐bis(3,5‐di‐chloro‐salicylidene)2,3‐diaminopy...

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Published in:European journal of inorganic chemistry 2020-02, Vol.2020 (5), p.480-490
Main Authors: Neshat, Abdollah, Kakavand, Meysam, Osanlou, Farzane, Mastrorilli, Piero, Schingaro, Emanuela, Mesto, Ernesto, Todisco, Stefano
Format: Article
Language:English
Subjects:
Acetic acid
Additives
Alcohols
Butyl hydroperoxide
Catalysts
Catalytic activity
Coordination compounds
Hydrogen peroxide
Imidazole
Imines
Inorganic chemistry
Ligands
Manganese
Optimization
Oxidation
Oxidizing agents
Schiff bases
Structure elucidation
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Summary:Asymmetric Schiff base manganese(III) complexes involving salen ligands, N,N'‐bis(salicylidene)2,3‐diaminopyridine, N,N'‐bis(3‐methoxysalicylidene)2,3‐diaminopyridine, N,N'‐bis(3,5‐di‐tert‐butylsalicylidene)2,3‐diaminopyridine and N,N'‐bis(3,5‐di‐chloro‐salicylidene)2,3‐diaminopyridine were prepared and their catalytic activity was investigated in the oxidation of some primary and secondary alcohols. During optimization of oxidation reactions, Mn‐4, bearing electron withdrawing N,N'‐Bis(3,5‐di‐chloro‐salicylidene)2,3‐diaminopyridine ligand, showed higher activity than other catalysts tested. The catalytic reactions were carried out in the presence of various oxidants such as oxygen, hydrogen peroxide or tert‐butyl hydroperoxide (TBHP) and additives such as acetic acid and imidazole. The oxidant/additive combination of TBHP and imidazole was shown to be effective for the oxidation process and the degree of their impact on oxidation reaction was found highly dependent on a balanced ratio between them. Mn‐4 was selected as the most effective catalyst under optimized reaction conditions and revealed efficient for the oxidation of secondary alcohols. Air stable manganese(III) catalysts with salen‐type ligands were prepared and applied as catalysts for the oxidation of a variety of primary and secondary alcohols. The Mn catalyst with electron‐withdrawing chloro substituents on the salen ligand was shown to be an efficient catalyst for oxidation reactions in the presence of imidazole and TBHP oxidant.
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.201901331