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Catalytic Activity of Chloro and Triflate Manganese(II) Complexes in Epoxidation Reactions: Reusable Catalytic Systems for Alkene Epoxidation
Author(s) -
Rich Jordi,
Manrique Ester,
Molton Florian,
Duboc Carole,
Collomb MarieNoëlle,
Rodríguez Montserrat,
Romero Isabel
Publication year - 2014
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201402032
Subject(s) - chemistry , acetonitrile , catalysis , trifluoromethanesulfonate , peracetic acid , manganese , electron paramagnetic resonance , imidazole , denticity , selectivity , medicinal chemistry , alkene , inorganic chemistry , ligand (biochemistry) , polymer chemistry , organic chemistry , hydrogen peroxide , biochemistry , physics , receptor , nuclear magnetic resonance , crystal structure
The catalytic oxidation of a series of alkenes by three Mn II complexes, MnCl 2 [(–)‐L] 2 ( 1 ), ({MnCl[(–)‐L]} 2 (μ‐Cl) 2 ) ( 2 ), and Mn(CF 3 SO 3 ) 2 [(–)‐L] 2 ( 3 ), having the bidentate N‐ligand (–)‐pinene[5,6]bipyridine, (–)‐L, and using peracetic acid as oxidant in acetonitrile is described. The performance of catalysts 1 and 2 is enhanced by the use of additives (NaHCO 3 and imidazole) and also using a [bmim]/acetonitrile mixture as reaction media. The latter conditions allow recyclability of the catalytic system, keeping good selectivity and conversion values in some cases. The nature of the species formed in acetonitrile after the addition of peracetic acid has been investigated through EPR and UV/Vis spectroscopy. The results point to the formation of high‐valent manganese species, among which a di‐μ‐oxo‐bridged Mn 2 (III,IV) binuclear species was unambiguously identified for complex 3 through a typical 16‐line EPR signature.