title: Dehydrogenative Coupling Reactions with Oxidized Guanidino-Functionalized Aromatic Compounds: Novel Options for σ-Bond Activation.
abstract: 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.
authors.affiliation: Anorganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Ute
authors.initials: U
authors.lastname: Wild
authors.affiliation: Anorganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Stefanie
authors.initials: S
authors.lastname: Federle
authors.affiliation: Anorganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Arne
authors.initials: A
authors.lastname: Wagner
authors.affiliation: Anorganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Elisabeth
authors.initials: E
authors.lastname: Kaifer
authors.affiliation: Anorganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany. hans-jorg.himmel@aci.uni-heidelberg.de.
authors.forename: Hans-Jörg
authors.initials: HJ
authors.lastname: Himmel
keywords: bond activation; coupling reactions; guanidine; redox chemistry