Project description
A toolbox for carbanion synthesis
Carbanions are organic ions carrying a negative charge on a carbon atom. Carbanionic compounds are important organometallic reagents commonly used as chemical intermediates. Their high reactivity and sensitivity to air and moisture limit the use of free carbanions in various chemical fields. The ERC-funded CarbFunction project aims to provide a new toolbox for the design of smart anionic reagents and catalysts. Through careful molecular design, carbanion reactivity will be controlled to enable their use as building blocks and functional groups. The newly formed carbanions will be tested in different applications: the stabilisation of main group species with unusual electronic properties, the design of bifunctional catalysts with abundant s- and p-block elements and the generation of versatile, weakly coordinating anions.
Objective
Carbanionic compounds such as organolithium or Grignard reagents are important organometallic reagents and commonly used in organic synthesis for difficult deprotonation or C-C bond formation reactions. Due to the strongly polarized metal carbon bond these reagents are usually highly reactive and sensitive towards air and moisture and thus must be handled under strictly anhydrous conditions. Owing to this intrinsic reactivity, carbanionic compounds are usually only prepared in situ and scarcely applied beyond their classical use as strong bases or alkylation reagents. Free carbanions without stabilizing metal-carbon inter¬action are usually even more reactive but can be isolated when being stabilized by electron withdrawing groups. These naked carbanions are isoelectronic to simple amines. Yet, whereas amines are applied in various fields of chemistry not only as bases but also as versatile building blocks and functional groups, applications of free carbanions are very limited.
This project will change the perspective on carbanionic compounds. By careful molecular design the reactivity of carbanions will be controlled to enable their use as broadly applicable building blocks and functional groups. Experimental and computational methods will provide a fundamental understanding of the electronic structure and its influencing factors, thus allowing for a systematic use of the anionic nature and donor capacity of carbanions to reach properties and reactivities, which are not accessible via conventional strategies. Thus, we will provide a new toolbox for the design of smart anionic reagents and catalysts. The power of this concept will be demonstrated by applying carbanions in different research directions ranging from the stabilization of main group species with unusual electronic properties, to designing new bifunctional catalysts with abundant s- and p-block elements and the generation of versatile weakly coordinating anions.
Fields of science
Programme(s)
- HORIZON.1.1 - European Research Council (ERC) Main Programme
Funding Scheme
ERC - Support for frontier research (ERC)Host institution
44801 Bochum
Germany