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

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2018

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Química "Profesor José Carlos Vílchez Martín"

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CIQSO

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http://hdl.handle.net/10272/15974

DOI

10.1002/anie.201807448

Abstract

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.

Keywords

Alkanes; C-H bond functionalization; Electrophilicity; Metal carbene complexes; Nucleophilicity

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Bibliographic citation

Olmos, A., Gava, R., Noverges, B., Bellezza, D., Jacob, K., Besora, M., Caballero Bevia, A., Pérez Romero, P. J. (2018). Measuring the Relative Reactivity of the Carbon-Hydrogen Bonds of Alkanes as Nucleophiles. Angewandte Chemie International Edition, 57(42), 13848-13852. https://doi.org/10.1002/anie.201807448

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