Abstract

Pyridines belong to the most abundant heteroarenes in medicinal chemistry and in agrochemical industry. In the lecture, highly regioselective pyridine C-H functionalization through a dearomatization/rearomatization sequence will be discussed. The dearomatized oxazino pyridines can be easily prepared on a large scale, and meta-functionalization becomes achievable through light-initiated radical alkylation and ionic transformations.1 As example, using such an approach meta-fluorinated pyridines are readily accessible.2 The same intermediates upon protonation to give the corresponding pyridinium salts also allow the highly regioselective radical Minisci para-alkylation.3,4 In addition, Cu-catalyzed meta-arylation5 and switchable radical para/meta-difluoromethylation6 through such intermediates will be presented. Radical meta-nitration7 and ionic meta-hydroxylation8 work equally well through such intermediates. Finally, it will be shown that this dearomatization concept is also applicable to pyridine skeletal editing.9 Further, it will be discussed that an alternative radical dearomatization process can be used for C to N mutation in indoles and benzofurans.10

References

1. Cao, H.; Cheng, Q.; Studer, A. Science 2022, 378, 779. For a review, see: Bhattacharya, D.; Haring, M.; Studer, A. Chimia 2025, 79, 476.

2. Haring, M.; Balanna, K.; Cheng, Q.; Lammert, J.; Studer, A. J. Am. Chem. Soc. 2024, 146, 30758

3. Cao, H.; Bhattacharya, D.; Cheng, Q., Studer, A. J. Am. Chem. Soc. 2023, 145, 15581.

4. Wang, Z.; Xu, P.; Studer, A. Org. Chem. Front. 2024, 11, 3849.

5. Guo, S.-M.; Xu, P.; Studer, A. Angew. Chem. Int. Ed. 2024, 63, e202405385.

6. Xu, P.; Wang, Z.; Guo, S.-M.; Studer, A. Nat. Commun. 2024, 15, 4121.

7. Balanna, K.; Studer, A. J. Am. Chem. Soc. 2025, 147, 7485.

8. Bhattacharya, D.; Studer, A. Angew. Chem. Int. Ed. 2025, 64, e202423512.

9. Cheng, Q.; Bhattacharya, D.; Haring, M.; Cao, H.; Mück-Lichtenfeld, C.; Studer, A. Nat. Chem. 2024, 16, 741.

10. Wang, Z.; Xu, P.; Guo, S.-M.; Daniliuc, C. G.; Studer, A. Nature 2025, 642, 92.

About the Speaker

Prof. Armido STUDER received his Diploma in 1991 and his PhD in 1995 from ETH Zürich under the direction of Prof. Dieter SEEBACH. He completed postdoctoral studies at the University of Pittsburgh with Prof. Dennis P. CURRAN. In 1996, he started his independent career at the ETH Zürich. In 2000, he was appointed as Associate Professor of Organic Chemistry at the Philipps-University Marburg and in 2004 as Full Professor (C4) of Organic Chemistry at the Westfälische- Wilhelms-University Münster. Since 2009, he has held a Full Professor (W3) position in Organic Chemistry at the University of Münster and has served as the Director of its Institute of Organic Chemistry.

Prof. Studer has been honored with a series of prestigious awards including the Gottfried Wilhelm Leibniz Prize (2026), the Adolf Von Baeyer Commemorative Medal (2025), the Paracelsus Prize of the Schweizerische Chemische Gesellschaft (2024), and the Arthur C. Cope Late Career Scholars Award (2024), among other notable recognitions. He has been elected as a member of the European Academy of Sciences, the Academia Europaea, and the German National Academy of Sciences, alongside his designation as a Fellow of The Royal Society of Chemistry.

For Attendees' Attention

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