Oxidative Carbon-Carbon Bond Cleavage by Vanadium Catalyst

The aerobic oxidative C?C bond cleavage of vicinal diols catalyzed by vanadium aminotriphenolates is described. Our results show that C?C bond cleavag e can be performed in different solvents,under an air or oxygen atmosphere, with a large variety of glycols (cyclic or linear, with aromati c or aliphaticsubstituents) affording the corresponding carbonyl derivatives with high chemoselectivity.Reactions can be performed with as little as 10 ppm of catalyst reaching TON up to 81,000 and TOFs of up to4150 h?1. A reaction mechanism, rationalized by de nsity functional theory calculations, is also proposed.

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Please use this identifier to cite or link to this collection: doi:10.19061/iochem-bd-1-53

This dataset derived results are published in:

Manuscript title: Efficient Vanadium-Catalyzed Aerobic C?C Bond OxidativeCleavage of Vicinal Diols

Journal: Adv. Synth. Catal.

DOI: https://doi.org/10.1002/adsc.201800050

PreviewTitleAuthor(s)ProgramCalculation typeMethod(s)Basis SetLinksEnergySolv.Vibr.Orb.
thumbnail.jpeg/Subs_Diol/TS-OV TS-OV-2González Fabra, JoanADF; 2016TSDFTTZ2P-
thumbnail.jpeg/Subs_Diol/IC ICGonzález Fabra, JoanADF; 2016Geometry optimization MinimumDFTTZ2P-
thumbnail.jpeg/Subs_Diol/Product ProductGonzález Fabra, JoanADF; 2016Geometry optimization TSDFTTZ2P-
thumbnail.jpeg/Subs_Diol/Guess_TS/Opt/Crash CrashGonzález Fabra, Joan-Single pointDFT--
thumbnail.jpeg/Subs_Diol/Guess_TS Guess_TSGonzález Fabra, JoanADF; 2016Single point TSDFTTZ2P-
thumbnail.jpeg/Subs_Diol/Diol DiolGonzález Fabra, JoanADF; 2016Geometry optimization MinimumDFTTZ2P-
thumbnail.jpeg/Subs_Diol/V_Product V_ProductGonzález Fabra, JoanADF; 2016Geometry optimizationDFTTZP-
thumbnail.jpeg/Subs_Diol/TS_CC/Freq FreqGonzález Fabra, JoanADF; 2016Single point TSDFTTZ2P-
thumbnail.jpeg/Subs_Diol/TS_CC TS_CCGonzález Fabra, JoanADF; 2016TSDFTTZ2P-
thumbnail.jpeg/Subs_Diol/Scan ScanGonzález Fabra, JoanADF; 2016Single pointDFTTZP-
thumbnail.jpeg/Subs_Diol/Chelate_Diol_Freq Chelate_Diol_FreqGonzález Fabra, JoanADF; 2016Single point MinimumDFTTZ2P-
thumbnail.jpeg/1V/TS-OV/Freq Freq-TSGonzález Fabra, JoanADF; 2016Single point TSDFTTZ2P-
thumbnail.jpeg/1V/TS-OV TS-OVGonzález Fabra, JoanADF; 2016TSDFTTZ2P-
thumbnail.jpeg/Solvent_Toluene/Chelate_Diol Chelate_DiolGonzález Fabra, JoanADF; 2016Single pointDFTTZ2P-
thumbnail.jpeg/Solvent_Toluene/Product ProductGonzález Fabra, JoanADF; 2016Single pointDFTTZ2P-
thumbnail.jpeg/Solvent_Toluene/Alk_Isom Alk_IsomGonzález Fabra, JoanADF; 2016Single pointDFTTZ2P-
thumbnail.jpeg/Solvent_Toluene/IC ICGonzález Fabra, JoanADF; 2016Single pointDFTTZ2P-
thumbnail.jpeg/Solvent_Toluene/IC_HOax IC_HOaxGonzález Fabra, JoanADF; 2016Single pointDFTTZ2P-
thumbnail.jpeg/Solvent_Toluene/IC_HLigand IC_HLigandGonzález Fabra, JoanADF; 2016Single pointDFTTZ2P-
thumbnail.jpeg/Solvent_Toluene/V2_O2 V2_O2González Fabra, JoanADF; 2016Single pointDFTTZ2P-
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