Publication Type Journal Article
Title Pronounced retention of stereoconfiguration upon sp(3) C-H bonds hydroxylation of dimethylcyclohexanes and decahydronaphthalenes with m-CPBA oxidant and a Co-phthalocyanine catalyst
Authors Dmytro S. Nesterov V Nesterova Maximilian N. Kopylovich Armando J.L. Pombeiro
Groups CCC
Journal MOLECULAR CATALYSIS
Year 2018
Month November
Volume 459
Number
Pages 8-15
Abstract A series of phthalocyanine (Pc) complexes of general formula (M(Pc)) (M = Mg, V, Mn, Fe, Co, Ni, Cu, Zn) was tested as catalysts for functionalization of sp(3) C-H bonds, namely in the mild stereoselective oxidation of cyclic alkanes (isomers of dimethylcyclohexane and decahydronaphthalene) using peroxides as oxidants. A high catalytic activity (yield of products up to 75\% based on the oxidant) and outstanding retention of stereo configuration of substrates (> 95\% for isomers of dimethylcyclohexane) was disclosed for the cobalt phthalocyanine catalyst [Co(Pc)] using m-chloroperbenzoic acid (m-CPBA) as oxidant and nitric acid as promoter. The phthalocyanine complexes other than Co are much less active with yields of products < 10\% and low stereo- and bond selectivities. The main reaction mechanism is proposed not to involve high-valent metal species, as evidenced by O-18-labeling and selectivity studies. The [Co(Pc)]/HNO3/m-CPBA system also catalyses chlorination and bromination of cyclohexane with HCl and N-bromosuccinimide as halogen sources.
DOI http://dx.doi.org/10.1016/j.mcat.2018.08.009
ISBN
Publisher
Book Title
ISSN 2468-8231
EISSN
Conference Name
Bibtex ID ISI:000447580300002
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