9 research outputs found
Decarboxylative Fluorination Strategies for Accessing Medicinally-relevant Products
Fluorinated organic compounds have a long history in medicinal chemistry, and synthetic methods to access target fluorinated compounds are undergoing a revolution. One powerful strategy for the installation of fluorine-containing functional groups includes decarboxylative reactions. Benefits of decarboxylative approaches potentially include: 1) readily available substrates or reagents 2) mild reaction conditions; 3) simplified purification. This focus review highlights the applications of decarboxylation strategies for fluorination reactions to access compounds with biomedical potential. The manuscript highlights on two general strategies, fluorination by decarboxylative reagents and by decarboxylation of substrates. Where relevant, examples of medicinally useful compounds that can be accessed using these strategies are highlighted
Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates
Trifluoroethylarenes are found in a variety of biologically active molecules, and strategies for accessing this substructure are important for developing therapeutic candidates and biological probes. Trifluoroethylarenes can be directly accessed via nucleophilic trifluoromethylation of benzylic electrophiles; however, current catalytic methods do not effectively transform electron-deficient substrates and heterocycles. To address this gap, we report a Cu-catalyzed decarboxylative trifluoromethylation of benzylic bromodifluoroacetates. To account for the tolerance of sensitive functional groups, we propose an inner-sphere mechanism of decarboxylation
Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates
Trifluoroethylarenes
are found in a variety of biologically active
molecules, and strategies for accessing this substructure are important
for developing therapeutic candidates and biological probes. Trifluoroethylarenes
can be directly accessed via nucleophilic trifluoromethylation of
benzylic electrophiles; however, current catalytic methods do not
effectively transform electron-deficient substrates and heterocycles.
To address this gap, we report a Cu-catalyzed decarboxylative trifluoromethylation
of benzylic bromodifluoroacetates. To account for the tolerance of
sensitive functional groups, we propose an inner-sphere mechanism
of decarboxylation