Synthesis of Dialkyl-Substituted Monofluoroalkenes via Palladium-Catalyzed Cross-Coupling of Alkyl Carbagermatranes

An unprecedented cross-coupling reaction of alkyl carbagermatranes with bromofluoroolefins to deliver dialkyl-substituted monofluoroalkenes was achieved. This cross-coupling reaction was performed under base/additive-free conditions with excellent functional group tolerance, therefore offering an opportunity for challenging dialkyl-substituted monofluoroalkenes. The preparation of bioactive agent analogues including an antitubercular agent mimic and a COX-2 inhibitor analogue and the late-stage fluoroalkenylation of drug-molecule derivatives proved the utility of this strategy.

Automated summary

An unprecedented cross-coupling reaction of alkyl carbagermatranes with bromofluoroolefins was achieved to deliver dialkyl-substituted monofluoroalkenes, providing an opportunity for challenging molecules with excellent functional group tolerance. The utility of this strategy was demonstrated through the preparation of bioactive agent analogues, including antitubercular agent mimics and COX-2 inhibitor analogues, as well as late-stage fluoroalkenylation of drug-molecule derivatives.