|
|
Divergent carbocatalytic routes in oxidative coupling of benzofused heteroaryl dimers : a mechanistic update |
|---|---|
| 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) |
| Persistent link: | http://urn.fi/urn:nbn:fi-fe2021041510500 |
| Language: | English |
| Published: |
John Wiley & Sons,
2021
|
| Publish Date: | 2021-04-15 |
| Description: |
AbstractMildly 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. see all
|
| 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 |
| OADOI: | https://oadoi.org/10.1002/chem.202005433 |
| Type of Publication: |
A1 Journal article – refereed |
| Field of Science: |
116 Chemical sciences |
| Subjects: | |
| 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. |
|
https://creativecommons.org/licenses/by-nc-nd/4.0/ |