University of Oulu

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.

Divergent carbocatalytic routes in oxidative coupling of benzofused heteroaryl dimers : a mechanistic update

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Author: Casadio, David S.1; Aikonen, Santeri1; Lenarda, Anna1;
Organizations: 1Department of Chemistry, University of Helsinki, A. I. Virtasen aukio 1, P.O. Box 55, 00014 Helsinki, Finland
2Research Unit of Sustainable Chemistry, Faculty of Technology, University of Oulu, 90014 Oulu, Finland
Format: article
Version: published version
Access: open
Online Access: PDF Full Text (PDF, 1.4 MB)
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Language: English
Published: John Wiley & Sons, 2021
Publish Date: 2021-04-15


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.

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Series: Chemistry. A European journal
ISSN: 0947-6539
ISSN-E: 1521-3765
ISSN-L: 0947-6539
Volume: 27
Issue: 16
Pages: 5283 - 5291
DOI: 10.1002/chem.202005433
Type of Publication: A1 Journal article – refereed
Field of Science: 116 Chemical sciences
Funding: Financial support from Academy of Finland [project no. 129062 (J.H.)] is acknowledged. The Finnish National Centre for Scientific Computing (CSC) is recognized for computational resources. D.S.C. is grateful to Magnus Ehrnrooth and Toso‐Montanari Foundations for funding, and M.Sc. Mikko Mäkelä for introduction into carbocatalysis and techniques to prepare our catalysts. We also thank Dr. Sami Heikkinen for assistance in NMR analysis.
Copyright information: © 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.