title: Iron Trichloride and Air Mediated Guanylation of Acylthioureas. An Ecological Route to Acylguanidines: Scope and Mechanistic Insights.
abstract: Recently we introduced iron trichloride as an environmentally benign and cost-efficient reagent for the synthesis of N-benzoylguanidines. This highly attractive synthetic approach grants access to a broad spectrum of N-benzoylguanidines under mild conditions in short reaction times. In this work we present an extended scope of our methodology along with the results obtained from mechanistic studies via in situ IR spectroscopy in combination with LC (liquid chromatography)-MS analyses. On the basis of these new mechanistic insights we were able to optimize the synthetic protocol and to develop an alternative mechanistic proposal. In this context the symbiotic roles of iron trichloride and oxygen in the guanylation process are highlighted.
authors.affiliation: Atotech Deutschland GmbH , Erasmusstrasse 20, D-10553 Berlin, Germany.
authors.forename: Simon
authors.initials: S
authors.lastname: Pape
authors.affiliation: Universität Potsdam , Institut für Chemie, Karl-Liebknecht-Straße 24-25, Haus 25, D-14476 Potsdam, Germany.
authors.forename: Pablo
authors.initials: P
authors.lastname: Wessig
authors.affiliation: Atotech Deutschland GmbH , Erasmusstrasse 20, D-10553 Berlin, Germany.
authors.forename: Heiko
authors.initials: H
authors.lastname: Brunner