Transition-Metal-Catalyzed Oxidative C(sp3)-H-Bond Functionalization - Rearrangement Tandem Reactions of Xanthenes and Acridines

Basic data for this project

Description

The project will be focused on the development of novel oxidative C(sp3)-H functionalization/tandem reactions of xanthenes and acridines with unexplored, unusual nucleophiles in oxidative C-H bond functionalization processes. Considering the growing demand on innovative and simple direct C-H bond transformations that lead to synthetically useful applications for both industry and academia, there is a need for the discovery of innovative oxidative C(sp3)-H bond coupling reactions and scope broadening. Therefore, the introduction of unprecedented combinations and reaction conditions, as well as unusual nucleophiles or reaction partners in this type of chemistry would be of great interest. In this project, a careful design of various combinations of reagents and oxidants will be conducted to be able to further couple the C-H functionalization step with other transformations such as ring expansions, rearrangements, additions or eliminations. This will allow the rapid introduction of a high grade of complexity from simple starting materials in a one-pot process. The uncommon nucleophiles that will be explored with xanthenes and acridines as chosen substrates comprise trimethylsilyl diazomethane derivatives (TMS-CR-N2), isonitriles (R-NC) or amines bearing a leaving group (RNH-LG). Consequently, we envision the development of cutting-edge methodologies for the synthesis of a number of different N- and O-heterocycles with interesting functional and/or bioactive properties such as substituted dibenzoazepines, dibenzodiazepinones or carboxamides.