Lecture by Hideki Yorimitsu, Department of Chemistry, Kyoto University
Aromatic Metamorphosis: Skeletal Transformations of Aromatic Rings
Info about event
Time
Location
iNANO AUD (1593-012)
Organizer
Hideki Yorimitsu
Host: Yonghui Zhang
Aromatic Metamorphosis: Skeletal Transformations of Aromatic Rings
Department of Chemistry, Kyoto University
Abstract
Aromatic skeletons are generally resistant to cleavage due to their high stabilization energy and strong endocyclic bonds. While exocyclic functionalizations are well explored, endocyclic modifications via partial disassembly and ring reconstruction remain less studied. Here, I disclose our efforts to establish 'aromatic metamorphosis',1 a strategy that transforms common aromatic compounds such as thiophenes, benzofurans, and indoles into distinct ring systems through multi-step or ideally single-step processes. Aromatic metamorphosis, or what we may now call skeletal editing2 of an aromatic ring, challenges traditional frameworks in organic chemistry and provides new efficient or sustainable tools for synthesizing otherwise inaccessible heterocycles and generating chemical libraries with diverse endocyclic frameworks.3,4
References
1. K. Nogi, H. Yorimitsu, Chem. Commun. 2017, 53, 4055; H. Yorimitsu, Acc. Chem. Res. 2025, 58, 1323.
2. a) J. Jurczyk, J. Woo, S. F. Kim, B. D. Dherange, R. Sarpong, M. D. Levin, Nat. Synth. 2022, 1, 352; b) B. W. Joynson, L. T. Ball, Helv. Chim. Acta 2023, 106, e202200182; c) M. D. Levin, Synlett 2024, 35, 1471.
3. Representative examples about endocyclic substitution: a) D. Vasu, H. Yorimitsu, A. Osuka, Angew. Chem. Int. Ed. 2015, 54, 7162; b) M. Bhanuchandra, K. Murakami, D. Vasu, H. Yorimitsu, A. Osuka, Angew. Chem. Int. Ed. 2015, 54, 10234; c) A. Kaga, K. Nogi, H. Yorimitsu, Chem. Eur. J. 2019, 25, 14780; d) T. Yanagi, T. Tanaka, H. Yorimitsu, Chem. Sci. 2021, 12, 2784.
4. Representative examples about insertion: a) H. Saito, S. Otsuka, K. Nogi, H. Yorimitsu, J. Am. Chem. Soc. 2016, 138, 15315; b) S. Tsuchiya, H. Saito, K. Nogi, H. Yorimitsu, Org. Lett. 2017, 19, 5557; c) S. Tsuchiya, H. Saito, K. Nogi, H. Yorimitsu, Org. Lett. 2019, 21, 3855.