Heterocycles are among the most frequently encountered scaffolds in drugs and pharmaceutically relevant substances. Among the plethora of available methods for their functionalization, the most appealing are those relying on a transition metals-catalyzed direct transformation of the C–H to C–C or C–Heteroatom bonds.
We have developed one-pot sequential multi-step approach to functionalization of aromatic and heterocyclic C–H bonds. The methodology comprises an initial reaction of electron-rich arenes or heteroarenes with a suitable I(III) reagent. The in situ formed unsymmetrical diaryl-λ3-iodanes subsequently undergo Cu or Pd-catalyzed reaction with wide range of oxygen and nitrogen nucleophiles.
5. Sokolovs, I.; Lubriks, D.; Suna, E. “Copper-Catalyzed Intermolecular C-H Amination of (Hetero)arenes via Transient Unsymmetrical-λ3-Iodanes” J. Am. Chem. Soc. 2014, 136, 6920–6928. DOI: 10.1021/ja502174d.
4. Lubriks, D.; Sokolovs, I.; Suna, E. “Indirect C–H Azidation of Heterocycles via Copper-Catalyzed Regioselective Fragmentation of Unsymmetrical λ3-Iodanes” J. Am. Chem. Soc. 2012, 134, 15436-15442. DOI: 10.1021/ja305574k