Cationic OrganoAcids: pushing the Limits for Applications in Synthesis – COALAS

Many important transformations in organic chemistry involve transient cationic intermediates where the nature of the associated anion is of utmost importance to control the reactivity and selectivities. In this project, we plan to focus on the development of cationic Brønsted organoacids that feature weakly coordinating anions for applications in the synthesis of (poly)cyclic compounds. To date, the protonation of very weak bases with the conjugate acids of such anions still represents a great challenge that we propose to overcome using in situ generated superacidic carbocations. By means of this methodology, new classes of cationic organoacids exhibiting very high acid strengths will be prepared and studied in-depth. These original charged organic species will be then considered for the activation of non polar functions such as unactivated C–C multiple bonds, which are beyond the reach of commonly used neutral organic acids. In that context, great efforts will be invested to develop stereoselective hydrofunctionalisation of unbiased olefins which represents a simple, atom- and step-economical yet challenging approach to generate molecular complexity.