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.
7. Sokolovs, I.; Suna, E. “Para-Selective Cu–catalyzed C–H Aryloxylation of Electron-rich Arenes and Heteroarenes” J. Org. Chem. 2016, 81, 371–379. DOI: 10.1021/acs.joc.5b02728
6. Berzina, B.; Sokolovs, I.; Suna, E. “Copper-Catalyzed para–Selective C–H Amination of Electron-Rich Arenes” ACS Catalysis 2015, 5, 7008–7014. DOI: 10.1021/acscatal.5b01992
5.“Copper-Catalyzed Intermolecular C-H Amination of (Hetero)arenes via Transient Unsymmetrical-λ3-Iodanes”, Sokolovs, I.; Lubriks, D.; Suna, E. J. Am. Chem. Soc. 2014, 136, 6920–6928. DOI: 10.1021/ja502174d.
4. “Indirect C–H Azidation of Heterocycles via Copper-Catalyzed Regioselective Fragmentation of Unsymmetrical λ3-Iodanes”, Lubriks, D.; Sokolovs, I.; Suna, E. J. Am. Chem. Soc. 2012, 134, 15436-15442. DOI: 10.1021/ja305574k
3. “Transition-Metal-Catalyzed Acetoxylation of Heterocycles: All that Glitters is not Palladium” (Highlight). Suna, E. Chem. Heterocycl. Comp. 2012, 48, 44-48. DOI: 10.1007/s10593-012-0967-5. Full Text
2. “Iodonium Salts Are Key Intermediates in Pd-Catalyzed Acetoxylation of Pyrroles”, Lubriks, D.; Sokolovs, I.; Suna, E. Org. Lett. 2011, 13, 4324–4327. DOI: 10.1021/ol201665c
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