Premium
Dehydrogenative Coupling Reactions with Oxidized Guanidino‐Functionalized Aromatic Compounds: Novel Options for σ‐Bond Activation
Author(s) -
Wild Ute,
Federle Stefanie,
Wagner Arne,
Kaifer Elisabeth,
Himmel HansJörg
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602236
Subject(s) - chemistry , kinetics , proton , coupling reaction , electron transfer , combinatorial chemistry , benzoquinone , photochemistry , polymer chemistry , organic chemistry , catalysis , physics , quantum mechanics
We present a new option for metal‐free σ‐bond activation, making use of oxidized, guanidino‐functionalized aromatic compounds (GFAs). We demonstrate this new option by the homocoupling reactions of thiols and phosphines. The kinetics and the reaction pathway were studied by a number of experiments (including heterocoupling of thiols and phosphines), supported by quantum‐chemical computations. Reaction of the oxidized GFA with p ‐dihydrobenzoquinone to give p ‐benzoquinone shows that typical proton‐coupled electron‐transfer reactions are also possible.