6533b857fe1ef96bd12b44e9

RESEARCH PRODUCT

Measuring the Relative Reactivity of the Carbon-Hydrogen Bonds of Alkanes as Nucleophiles

Andrea OlmosKane JacobPedro J. PérezAna CaballeroBárbara NovergesGregorio AsensioRiccardo GavaMaria BesoraFeliu MaserasMichel EtienneW. M. Chamil SameeraDelia Bellezza

subject

Alkanechemistry.chemical_classificationC-H bond functionalization010405 organic chemistryHydrogen bondNucleophilicitychemistry.chemical_elementGeneral MedicineGeneral Chemistry010402 general chemistry01 natural sciencesMedicinal chemistryCatalysis0104 chemical scienceschemistryNucleophileAlkanes[CHIM.COOR]Chemical Sciences/Coordination chemistryReactivity (chemistry)ElectrophilicityCarbonMetal carbene complexes

description

We report quantitative measurements of the relative reactivities of a series of C-H bonds of gaseous or liquid CnH2n+2 alkanes (n = 1-8, 29 different C-H bonds) towards insitu generated electrophiles (copper, silver, and rhodium carbenes), with methane as the reference. This strategy surpasses the drawback of previous model reactions of alkanes with strong electrophiles suffering from C-C cleavage processes, which precluded direct comparison of the relative reactivities of alkane C-H bonds.

yearjournalcountryeditionlanguage
2018-01-01
10.1002/anie.201807448http://hdl.handle.net/10272/15974