Intramolecular C[BOND]H Bond Activation through a Flexible Ester Linkage

Authors

  • Dr. Christopher J. Shaffer,

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo námĕstí 2, 16610 Prague 6 (Czech Republic)
    Search for more papers by this author
  • Dr. Detlef Schröder,

    Corresponding author
    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo námĕstí 2, 16610 Prague 6 (Czech Republic)
    • Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo námĕstí 2, 16610 Prague 6 (Czech Republic)
    Search for more papers by this author
  • Christoph Gütz,

    1. Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany)
    Search for more papers by this author
  • Prof. Dr. Arne Lützen

    Corresponding author
    1. Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany)
    • Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany)
    Search for more papers by this author

  • This work was supported by the Academy of Sciences of the Czech Republish (RVO 61388963) and the European Research Council (AdG HORIZOMS).

Abstract

original image

Replacing the director: A bipyridinyl ligand with an aliphatic side chain determines the regioselectivity of copper-catalyzed C[BOND]H oxidation by intramolecular effects. Because the aliphatic chain is attached through an ester linkage, the catalytic cycle can in principle be closed by transesterification. Ion-mobility mass spectrometry and isotopic labeling provide mechanistic insight not available from direct mass spectrometry experiments.

Ancillary