Carbocatalytic cascade synthesis of polysubstituted quinolines from aldehydes and 2-vinyl anilines
Mäkelä, Mikko K.; Bulatov, Evgeny; Malinen, Kiia; Talvitie, Juulia; Nieger, Martin; Melchionna, Michele; Lenarda, Anna; Hu, Tao; Wirtanen, Tom; Helaja, Juho (2021-08-04)
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
© 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/
https://urn.fi/URN:NBN:fi-fe2021090244975
Tiivistelmä
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.
Kokoelmat
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