Vittorio Pace vi invita al seminario:
Aromatic Metamorphosis
di Hideki Yorimitsu, Kyoto University, Japan
Il seminario si terrà venerdì 10 ottobre p.v. alle ore 15.00 in Sala Parravano, edificio Cannizzaro (CU014).
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 editing [2] 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] a) H. Yorimitsu, D. Vasu, M. Bhanuchandra, K. Murakami, A. Osuka, Synlett 2016, 27, 1765; b) K. Nogi, H. Yorimitsu, Chem. Commun. 2017, 53, 4055. c) 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.
[3] 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) M. Bhanuchandra, H. Yorimitsu, A. Osuka, Org. Lett. 2016, 18, 384; e) M. Onoda, Y. Koyanagi, H. Saito, M. Bhanuchandra, Y. Matano, H. Yorimitsu, Asian J. Org. Chem. 2017, 6, 257; f) T. Furukawa, T. Yanagi, A. Kaga, H. Saito, H. Yorimitsu, Helv. Chim. Acta 2021, 104, e202100195; g) T. Yanagi, T. Tanaka, H. Yorimitsu, Chem. Sci. 2021, 12, 2784.
[4] 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.
Short Biography:
2015- Professor, Department of Chemistry, Kyoto Univ.
2009-15 Associate Professor, Department of Chemistry, Kyoto Univ.
2008-09 Associate Professor, Department of Material Chemistry, Kyoto Univ.
2003-08 Assistant Professor, Department of Material Chemistry, Kyoto Univ.
2002-03 JSPS Postdoctoral Fellow, Univ. Tokyo (with Prof. Eiichi Nakamura)
2002 PhD, Kyoto Univ. (with Prof. Koichiro Oshima)
1997 BS, Kyoto Univ.
Recent Additional Service:
2019- Associate Editor, SYNTHESIS, Thieme
2019- Project Leader, CREST, Japan Science and Technology Agency (JST)
2025- Vice-Chair, Organic Chemistry Division, The Chemical Society of Japan
2025 Co-Chair, OMCOS-22 (September 1-5, 2025, 22nd IUPAC International Symposium on Organometallic Chemistry Directed towards Organic Synthesis)
Recent Awards/Recognitions:
2024 Distinguished Professor of Science, Hong Kong Baptist University
2023 Swiss Chemical Society Lectureship Award
2020 Japan Academy Medal
2020 JSPS Prize
2018 Negishi Award (from JST)
2016 Mukaiyama Award (from Synth. Org. Chem. Soc. Jpn.)
2011 The Young Scientists’ Prize (from the MEXT Minister)
Research Interest:
organic synthesis, organometallic chemistry, carbanion chemistry, transition metal catalysts, synthetic
radical chemistry, organosulfur chemistry, aromatic metamorphosis
Key Accounts/Reviews:
“Aromatic Metamorphosis: Skeletal Editing of Aromatic Rings”
Acc. Chem. Res. 2025, 58, 1323–1334.
“Utilization of Silanols in Transition Metal-Catalyzed Organic Synthesis”
ACS Catal. 2023, 13, 7472–7487.
“Sulfonium-aided coupling of aromatic rings via sigmatropic rearrangement”
Proc. Jpn. Acad., Ser. B 2022, 98, 190–205.
“Carbon–Carbon Bond Cleavage at Allylic Positions: Retro-allylation and Deallylation”
Chem. Rev. 2021, 121, 345–364.
“Catalytic Transformations of Sulfonium Salts via C–S Bond Activation”
Chem. Rec. 2021, 21, 3356–3369.
“Catalytic C-H Arylation of Tetrathiafulvalenes for the Synthesis of Functional Materials”
Synthesis 2020, 52, 3326–3336.
“C–S Bond Activation”
Top. Curr. Chem. 2018, 376, No. 13.
“Aromatic metamorphosis: conversion of an aromatic skeleton into a different ring system”
Chem. Commun. 2017, 53, 4055–4065.