TY - JOUR
T1 - Dioxomolybdenum(VI) complexes containing chiral oxazolines applied in alkenes epoxidation in ionic liquids: A highly diastereoselective catalyst
AU - Cantabrana, Beatriz Royo
PY - 2011/1/1
Y1 - 2011/1/1
N2 - New monometallic dioxomolybdenum complexes, 2 and 3, containing the bis(oxazoline) B and the oxazolinyl-pyridine C respectively, have been prepared and fully characterized both in solution and solid state, including the single-crystal X-ray diffraction analysis for 2, which represents the first structure of a Mo(VI) complex coordinated to a bis(oxazoline). These complexes, together with the bimetallic system 1, were used as catalytic precursors for alkenes epoxidation (cyclooctene, (R)-limonene, trans-beta-methylstyrene) in imidazolium- and pyrrolidinium-based ionic liquids, exhibiting a high chemoselectivity towards the epoxide formation, mainly for cyclooctene and (R)-limonene epoxidation, without formation of the corresponding diols. In [BMP][NTf2] (BMP=butyl methyl pyrrolidinium: NTf2 = bis(trifluoromethanesulfonyl)amide), complex 1 exclusively gave trans(R)-limonene 1,2-epoxide, while monometallic catalytic systems led to a low diastereoselectivity. Mo-95 NMR studies helped to understand the catalytic behaviour of 1 and 2 in ionic liquid medium
AB - New monometallic dioxomolybdenum complexes, 2 and 3, containing the bis(oxazoline) B and the oxazolinyl-pyridine C respectively, have been prepared and fully characterized both in solution and solid state, including the single-crystal X-ray diffraction analysis for 2, which represents the first structure of a Mo(VI) complex coordinated to a bis(oxazoline). These complexes, together with the bimetallic system 1, were used as catalytic precursors for alkenes epoxidation (cyclooctene, (R)-limonene, trans-beta-methylstyrene) in imidazolium- and pyrrolidinium-based ionic liquids, exhibiting a high chemoselectivity towards the epoxide formation, mainly for cyclooctene and (R)-limonene epoxidation, without formation of the corresponding diols. In [BMP][NTf2] (BMP=butyl methyl pyrrolidinium: NTf2 = bis(trifluoromethanesulfonyl)amide), complex 1 exclusively gave trans(R)-limonene 1,2-epoxide, while monometallic catalytic systems led to a low diastereoselectivity. Mo-95 NMR studies helped to understand the catalytic behaviour of 1 and 2 in ionic liquid medium
KW - CYCLOOCTENE
KW - OXIDES
KW - OLEFIN EPOXIDATION
KW - ORGANORHENIUM(VII)
KW - ORGANOMOLYBDENUM(VI)
KW - LIGANDS
KW - OXIDATION
KW - PHASE
U2 - 10.1016/j.apcata.2011.03.024
DO - 10.1016/j.apcata.2011.03.024
M3 - Article
VL - 398
SP - 88
EP - 95
JO - Applied Catalysis A-General
JF - Applied Catalysis A-General
SN - 0926-860X
IS - 1-2
ER -