Decarboxylative C-C cross coupling reactions based on Copper Photoredox Catalysis

• Applicant: Dr. Alexander Haseloer
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation ; Inorganic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2022 to 2024
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 504634372

This year, David MacMillan's group presented a very gentle and cost-effective method for the in situ preparation of aryl radicals. Their method is characterized by the use of copper as a catalyst and carboxylic acids as starting agents. A copper carboxylate complex formed in this methodology decomposes with the elimination of CO2 and releases the highly reactive aryl radicals. Aryl radicals are of great interest in organic chemistry as synthesis building blocks and have already been used in the past in a wide variety of reactions. Synthesis via copper-catalyzed photoredox catalysis can help to produce cost-effective catalytic systems for a wide variety of reactions under mild conditions.Based on the work of the MacMillan group, the substrate tolerance of the reaction has been tested with respect to halogenation reactions. It has already been shown how diverse the field of the reaction is. In the course of evaluating the reaction mechanism, a so-called Giese product was also obtained, thus already opening the door to C-C linkage reactions.C-C cross-coupling reactions have been known in the literature for more than 100 years and could so far often only be realized if the system is exposed to harsh conditions or if a usually expensive cocatalyst, often of palladium-based structures, is used. The methodology now described enables the knotting reaction under mild conditions and high cost efficiency. The methodology now to be developed can draw on a large body of already established work on aryl radicals and, because of the mild conditions, use a large substrate group to develop new cost-effective C-C cross-coupling reactions.

• DFG Programme: WBP Fellowship
• International Connection: USA
• Host: Professor David W. C. MacMillan, Ph.D.