Back to Search
Start Over
Stereoselective oxidation of alkanes with m-CPBA as an oxidant and cobalt complex with isoindole-based ligands as catalysts
- Source :
- RSC Advances. 6:93756-93767
- Publication Year :
- 2016
- Publisher :
- Royal Society of Chemistry (RSC), 2016.
-
Abstract
- Two complexes with isoindole-core ligands of general formula [M{C6H4C(NH2)NC(ONCMe2)2}2](NO3)2 (M = Co for 1 and M = Ni for 2) were studied as catalysts for the mild stereoselective alkane oxidation with m-chloroperbenzoic acid (m-CPBA) as an oxidant and cis-1,2-dimethylcyclohexane (cis-1,2-DMCH) as a main model substrate. Complex 1 disclosed a pronounced activity, with high retention of stereoconfiguration of substrates (>98% for cis-1,2-DMCH) and highest cis/trans ratio of tertiary alcohols (products) of 56, under mild conditions. The best achieved yields of tertiary cis-alcohols were of 13.7 and 50.5%, based on the substrate (cis-1,2-DMCH) and the oxidant (m-CPBA) respectively. Kinetic experiments, high bond and stereoselectivity parameters, kinetic isotope effect of 7.2(2) in the oxidation of cyclohexane, and incorporation of 18O from H218O support the involvement of CoIVO high-valent metal–oxo intermediates as main C–H attacking species.
- Subjects :
- Alkane
chemistry.chemical_classification
Cyclohexane
010405 organic chemistry
General Chemical Engineering
Substrate (chemistry)
chemistry.chemical_element
General Chemistry
010402 general chemistry
01 natural sciences
Medicinal chemistry
0104 chemical sciences
Catalysis
chemistry.chemical_compound
chemistry
Kinetic isotope effect
Organic chemistry
Stereoselectivity
Isoindole
Cobalt
Subjects
Details
- ISSN :
- 20462069
- Volume :
- 6
- Database :
- OpenAIRE
- Journal :
- RSC Advances
- Accession number :
- edsair.doi...........0008942ac20c8b5ca66d9262f5abb0ec
- Full Text :
- https://doi.org/10.1039/c6ra14382b