21985-86-4Relevant articles and documents
Use of CuO encapsulated in mesoporous silica SBA-15 as a recycled catalyst for allylic C-H bond oxidation of cyclic olefins at room temperature
Samadi, Saadi,Ashouri, Akram,Ghambarian, Mehdi
, p. 19330 - 19337 (2017)
CuO nanoparticles were deposited on SBA-15 in three routes. These were metal loading on SBA-15 and calcination at 550 °C (Cu-SBA-15), metal loading on 3-aminopropyl-trimethoxysilane grafted SBA-15 and calcination at 550 °C (Cu-N-SBA-15), and metal loading
2-Aminopyrazine-functionalized MCM-41 nanoporous silica as a new efficient heterogeneous ligand for Cu-catalyzed allylic C–H bonds oxidation of olefins
Samadi, Saadi,Ashouri, Akram,Kamangar, Shadi,Pourakbari, Fatemeh
, p. 557 - 569 (2019/11/03)
In spite of the importance of the application of allylic C–H bond oxidation of olefins in organic synthesis and existence of the numerous reports, lots of limitations such as large excess of the olefin respect to the oxidant, low chemical yield, long time of reaction and a large amount of the catalyst were reminded. We introduced a novel catalytic system using functionalized MCM-41 as catalyst support to promote efficiency of this reaction. The heterogeneous ligand Pyr-MCM-41 was prepared by substituted 2-aminopyrazine ligand on functionalized MCM-41 with 3-chloropropyltrimthoxysilane and characterized by FT-IR, XRD, SEM, EDX, BET, TGA, CHN techniques. In situ immobilized Pyr-MCM-41 by copper (I) trifluoromethanesulfonate (CuOTf) was applied in direct catalytic esterification of inert C–H bonds in olefins using various peresters at room temperature.
The Influence of Remote Heteroatom Substituents on the Stereoselectivity of Cyclopentene Ozonolysis
Bunnelle, William H.,Isbell, Terry A.
, p. 729 - 740 (2007/10/02)
The stereoselectivity for ozonide formation from cyclopentenes with allylic heteroatom substituents has been examined.Silyl ethers give high selectivity in favor of the exo-substituted ozonide, while esters of 2-cyclopentenol form ozonide mixtures with little stereoselection.Trapping experiments establish that fragmentation of the primary ozonides is highly regioselective to give only one of the isomeric ω-oxo carbonyl oxide intermediates and that the variation in final ozonide stereochemistry results from differing interactions between the remote substituent groupsand the carbonyl oxide system during cyclization of this intermediate.The effect of substituent and solvent on ozonide stereochemistry suggests a dominant role for electrostatic repulsion between carbonyl oxide and the heteroatom substituent during intramolecular cycloaddition.A chair-like transition state is proposed for this process and is in accord with the increase in exo selectivity for derivatives of 2-methyl-2-cyclopentenol.