Divergent carbocatalytic routes in oxidative coupling of benzofused heteroaryl dimers : a mechanistic update
Casadio, David S.; Aikonen, Santeri; Lenarda, Anna; Nieger, Martin; Hu, Tao; Taubert, Stefan; Sundholm, Dage; Muuronen, Mikko; Wirtanen, Tom; Helaja, Juho (2021-03-18)
Casadio, David S.
Aikonen, Santeri
Lenarda, Anna
Nieger, Martin
Hu, Tao
Taubert, Stefan
Sundholm, Dage
Muuronen, Mikko
Wirtanen, Tom
Helaja, Juho
John Wiley & Sons
18.03.2021
D. S. Casadio, S. Aikonen, A. Lenarda, M. Nieger, T. Hu, S. Taubert, D. Sundholm, M. Muuronen, T. Wirtanen, J. Helaja, Chem. Eur. J. 2021, 27, 5283. https://doi.org/10.1002/chem.202005433
https://creativecommons.org/licenses/by-nc-nd/4.0/
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
https://creativecommons.org/licenses/by-nc-nd/4.0/
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
https://creativecommons.org/licenses/by-nc-nd/4.0/
Julkaisun pysyvä osoite on
https://urn.fi/URN:NBN:fi-fe2021041510500
https://urn.fi/URN:NBN:fi-fe2021041510500
Tiivistelmä
Abstract
Mildly thermal air or HNO₂ oxidized activated carbons catalyse oxidative dehydrogenative couplings of benzo[b]fused heteroaryl 2,2’‐dimers, e.g., 2‐(benzofuran‐2‐yl)‐1H‐indole, to chiral 3,3’‐coupled cyclooctatetraenes or carbazole‐type migrative products under O₂ atmosphere. DFT calculations show that the radical cation and the Scholl‐type arenium cation mechanisms lead to different products with 2‐(benzofuran‐2‐yl)‐1H‐indole, being in accord with experimental product distributions.
Kokoelmat
- Avoin saatavuus [32003]