Strongly Polarized Carbon: Taming Fundamental Intermediates and Their Applications

ongoing

In CC-CHARGED, I propose a new concept to induce C–C bond polarization as well as predict fundamentally new stable carbon-based compound classes. The manipulation of functional groups builds the basis for the rational design of complex molecules in organic synthesis. While most compound classes have been studied for decades, few remain virtually unexplored, only suggested as reactive intermediates. I propose to tame these elusive intermediates into hitherto unknown room-temperature stable compound classes. Central motif to gain stability relies in the polarization of the C–C bond, which can either result in zwitterions (charged +/-) or diradicals. The dichotomic behavior will be analyzed and a general approach to C–C bond polarization will be developed based on a new concept of mesoionic frustration. Such mesoions are predicted to be exceptionally strong polarized carbon compounds, exceeding the polarization of traditional ylides, triggering applications from transition metal, main group chemistry to organic synthesis. The reactivity of such strong carbon donors will be analyzed, correlated and a scale generated. Applications of C–C bond polarization in the stabilization of unsaturated diazo and monosubstituted carbon compounds are presented. Their synthesis, electronic structure and reactivity will be evaluated and applications such as C-atom transfer reagents for molecular editing studied. While singlet vinylidenes are central intermediates in organic reactions, the generation and reactivity of triplet vinylidenes is virtually unknown. I propose them as new compounds in organic chemistry, as metal-vinylidene precursors and as new platforms for magnetic applications. Recent high-impact publications by the group build the basis for this project that goes far beyond the state-of-the-art. Considering that carbon is the pivotal element of life and the central element of organic chemistry, CC-CHARGED is a fundamental, ground-breaking contribution to organic chemistry.