Our research interests are focused on the design of new catalytic tools and their use in the development of practical and efficient methods for the construction of molecules of various interest.
Homogeneous gold catalysis is a specific and powerful synthetic tool for the efficient functionalization of carbon π-systems and for the
generation of molecular complexity and diversity. The ability of electrophilic gold complexes to selectively bind to alkynes or allenes in the presence of other functional groups, and to activate them towards their functionalization by a variety of nucleophilic species, provides a unique opportunity for the discovery of novel transformations. In addition to its acidic character, gold can potentially act as an electron donor, thus allowing the stabilization of intermediate cationic species and favoring reaction pathways not accessible with other Lewis acids. Advantageously, gold complexes are also non-toxic, tolerant to oxygen and compatible with aqueous conditions, thus allowing their practical manipulation and potential use in environmentally friendly industrial processes.
Our group is exploiting the unique reactivity of electrophilic gold complexes for the discovery of novel and useful reactions that may apply to various areas of organic synthesis.
New Gold Catalysts
The synthesis of new gold catalysts is of main importance in order to improve the efficiency and selectivity of reactions, access novel reactivity and modulate the behavior of gold intermediates in synthetic transformations. Our group is active in this area and has developed several families of gold(I) complexes which are now largely employed as catalysts by research groups working in the field of homogeneous gold catalysis.
Cyclizations - Multiple Bond Forming Transformations
By taking advantage of the unique reactivity of electrophilic gold species, our group designs and develops catalytic processes allowing for the formation of multiple C–C and/or C-heteroatom bonds in a single operation and in a stereoselective manner.
Nitrene transfers onto carbon π-systems
Nitrogen nucleophilic partners possesing a leaving group can be used in gold catalysis to formally transfer a nitrene species on a carbon π-system. We exploit such types of reactivity to develop processes allowing for the synthesis of various nitrogen containing heterocycles by aminofunctionalization of alkyne and allene motifs.
Hydrogen transfer processes
Hydrogen transfer, whether formally as a hydride (H-) under electrophilic activation or as a hydrogen
radical (H∙), represents a useful method to functionalize organic molecules and increase their structural complexity. While many transformations involving these processes have been reported over the years, this reactivity remains under exploited in the context of synthetic methodology. Using gold catalysis or radical chemistry, we design and develop transformations allowing the hydrofunctionalization of carbon π-systems (alkenes, alkynes and allenes) and/or the functionalization of C-H bonds.
Hydride transfer processes
Gold catalysis, which allows for the generation of highly electrophilic intermediates, represents a particularly useful tool to perform hydride transfers. Our group exploits this property in the development of transformations that involve intramolecular hydride shifts on gold-activated alkynes and allenes or on electrophilic gold intermediates.
Radical hydrogen transfer
We are also employing radical chemistry under redox conditions to develop transformations involving intermediate H-transfer steps. We are more especially interested in reactions allowing the regio- and diastereoselective hydrofunctionalization of alkenes.