University of Oulu

M. K. Mäkelä, E. Bulatov, K. Malinen, J. Talvitie, M. Nieger, M. Melchionna, A. Lenarda, T. Hu, T. Wirtanen, J. Helaja, Adv. Synth. Catal. 2021, 363, 3775, https://doi.org/10.1002/adsc.202100711

Carbocatalytic cascade synthesis of polysubstituted quinolines from aldehydes and 2-vinyl anilines

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Author: Mäkelä, Mikko K.1; Bulatov, Evgeny1; Malinen, Kiia1;
Organizations: 1Department of Chemistry, University of Helsinki, A.I. Virtasen aukio 1, 00014 Helsinki, Finland
2Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via L. Giorgieri 1, 34127 Trieste, Italy
3Research Unit of Sustainable Chemistry, Faculty of Technology, University of Oulu, FI-, 90014 Oulu, Finland
Format: article
Version: published version
Access: open
Online Access: PDF Full Text (PDF, 5.5 MB)
Persistent link: http://urn.fi/urn:nbn:fi-fe2021090244975
Language: English
Published: John Wiley & Sons, 2021
Publish Date: 2021-09-02
Description:

Abstract

Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold.

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Series: Advanced synthesis & catalysis
ISSN: 1615-4150
ISSN-E: 1615-4169
ISSN-L: 1615-4150
Volume: 363
Issue: 15
Pages: 3775 - 3782
DOI: 10.1002/adsc.202100711
OADOI: https://oadoi.org/10.1002/adsc.202100711
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.
Copyright information: © 2021 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
  https://creativecommons.org/licenses/by/4.0/