Within the presented project proposal the possibility of the arylation of sp3 C-H bonds via the methodology of C-
H activation shall be investigated. Based on the successful arylation of N-phenylpyrrolidine it is aimed to expand
this method to cyclic BOC-protected amines such as piperidine, piperazine, morpholine, nipecotic acid ester, and
others as representative substrates.
The key step of the envisioned reaction sequence is the selective arylation of the BOC protected amines via
activation of the sp3 C-H bond adjacent to the protected nitrogen.
These direct arylation reactions of cyclic amines are of significant importance since the obtained structural motifs
of arylated cyclic amines can be found in naturally occurring alkaloids and biologically active compounds.
In the course of the project an effective catalyst/solvent/base system has to be established for these transformations
whereby preliminary results from the Sames group on related problems can be used as starting point. Subsequently,
reactions shall be optimized with respect to yield, catalyst (metal center, ligands), catalyst loading, substrate scope,
temperature, and time. In the optimization process mechanistic studies will be included to get more detailed
information on the reaction pathway. This information will then be used for further improvement of the catalytic
system. Tuning of the catalyst will address special needs of the reaction regarding the slow step of the catalytic
cycle. Intelligent changing of the electronic and steric properties of the ligands and/or the center metal of the
catalyst is expected to lead to an improved reaction outcome.