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Issue 96, 2016, Issue in Progress
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Stereoselective oxidation of alkanes with m-CPBA as an oxidant and cobalt complex with isoindole-based ligands as catalysts

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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 CoIV[double bond, length as m-dash]O high-valent metal–oxo intermediates as main C–H attacking species.

Graphical abstract: Stereoselective oxidation of alkanes with m-CPBA as an oxidant and cobalt complex with isoindole-based ligands as catalysts

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Publication details

The article was received on 02 Jun 2016, accepted on 23 Sep 2016 and first published on 26 Sep 2016


Article type: Paper
DOI: 10.1039/C6RA14382B
Citation: RSC Adv., 2016,6, 93756-93767
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    Stereoselective oxidation of alkanes with m-CPBA as an oxidant and cobalt complex with isoindole-based ligands as catalysts

    O. V. Nesterova, M. N. Kopylovich and D. S. Nesterov, RSC Adv., 2016, 6, 93756
    DOI: 10.1039/C6RA14382B

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