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

Andrea Olmos, Riccardo Gava, Bárbara Noverges, Delia Bellezza, Kane Jacob, Maria Besora, W. M.Chamil Sameera, Michel Etienne, Feliu Maseras, Gregorio Asensio, Ana Caballero, Pedro J. Pérez

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21 Citations (Scopus)

Abstract

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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 in situ 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.
Original languageEnglish
Pages (from-to)13848-13852
JournalAngewandte Chemie - International Edition
Volume57
DOIs
Publication statusPublished - 15 Oct 2018

Keywords

  • alkanes
  • C−H bond functionalization
  • electrophilicity
  • metal carbene complexes
  • nucleophilicity

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