Publication - Journal Article Direct functionalization of C−H bonds by electrophilic anions

Proceedings of the National Academy of Sciences, vol. 117, iss. 38, pp. 23374-23379, 2020

Jonas Warneke, Martin Mayer, Markus Rohdenburg, Xin Ma, Judy K. Y. Liu, Max Grellmann, Sreekanta Debnath, Vladimir A. Azov, Edoardo Aprà, Robert P. Young, Carsten Jenne, Grant E. Johnson, Hilkka I. Kenttämaa, Knut R. Asmis, Julia Laskin

Significance Functionalization of unreactive molecules is a significant chemical challenge relevant to the conversion of abundant feedstocks such as alkanes into high-value chemicals. Herein, we demonstrate a new mechanism of alkane functionalization by the substitution of a proton by an anion in an alkyl chain. The reactive anion used for this reaction is generated from a highly stable precursor. The reaction mechanism is established using experimental and computational approaches, and the products are collected in the condensed phase using high-flux mass-selected ion deposition. This paves the way for exploiting the properties of gaseous ions for the generation of complex molecular structures in the condensed phase.