University of Oulu

T. Wirtanen, S. Aikonen, M. Muuronen, M. Melchionna, M. Kemell, F. Davodi, T. Kallio, T. Hu, J. Helaja, Chem. Eur. J. 2019, 25, 12288. https://doi.org/10.1002/chem.201903054

Carbocatalytic oxidative dehydrogenative couplings of (hetero)aryls by oxidized multi-walled carbon nanotubes in liquid phase

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Author: Wirtanen, Tom1; Aikonen, Santeri2; Muuronen, Mikko3;
Organizations: 1Department of Chemistry, UniveDepartment of Chemistry, University of Helsinki, A. I. Virtasen aukio1, P.O. Box 55, 00014 Helsinki (Finland)rsity of Helsinki
2Department of Chemistry, University of HeDepartment of Chemistry, University of Helsinki, A. I. Virtasen aukio1, P.O. Box 55, 00014 Helsinki (Finland)lsinki
3Department of Chemistry, University of Helsinki, A. I. Virtasen aukio1, P.O. Box 55, 00014 Helsinki (Finland)
4Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via L. Giorgieri 1, 34127 Trieste (Italy)
5Department of Chemistry and Materials Science, Aalto University, P.O Box 16100, 00076 Aalto (Finland)
6Research Unit of Sustainable Chemistry, Faculty of Technology, University of Oulu, 90014 Oulu (Finland)
Format: article
Version: accepted version
Access: embargoed
Persistent link: http://urn.fi/urn:nbn:fi-fe2019103035869
Language: English
Published: John Wiley & Sons, 2019
Publish Date: 2020-07-23
Description:

Abstract

HNO3‐oxidized carbon nanotubes catalyze oxidative dehydrogenative (ODH) carbon–carbon bond formation between electron‐rich (hetero)aryls with O2 as a terminal oxidant. The recyclable carbocatalytic method provides a convenient and an operationally easy synthetic protocol for accessing various benzofused homodimers, biaryls, triphenylenes, and related benzofused heteroaryls that are highly useful frameworks for material chemistry applications. Carbonyls/quinones are the catalytically active site of the carbocatalyst as indicated by model compounds and titration experiments. Further investigations of the reaction mechanism with a combination of experimental and DFT methods support the competing nature of acid‐catalyzed and radical cationic ODHs, and indicate that both mechanisms operate with the current material.

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Series: Chemistry. A European journal
ISSN: 0947-6539
ISSN-E: 1521-3765
ISSN-L: 0947-6539
Volume: 25
Issue: 53
Pages: 12288 - 12293
DOI: 10.1002/chem.201903054
OADOI: https://oadoi.org/10.1002/chem.201903054
Type of Publication: A1 Journal article – refereed
Field of Science: 116 Chemical sciences
215 Chemical engineering
216 Materials engineering
221 Nanotechnology
Subjects:
Funding: Financial support from Academy of Finland [project no. 129062 (J.H.)] is acknowledged
Copyright information: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version of the following article: T. Wirtanen, S. Aikonen, M. Muuronen, M. Melchionna, M. Kemell, F. Davodi, T. Kallio, T. Hu, J. Helaja, Chem. Eur. J. 2019, 25, 12288, which has been published in final form at https://doi.org/10.1002/chem.201903054. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.