Thomas G.F. Marsh
HFO‐1234yf as a CF3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones
Marsh, Thomas G.F.; Santambrogio, Alessia; Murray, Ben J.; Boulton, Lee T.; Aguilar, Juan A.; Yufit, Dmitry S.; Sandford, Graham; Brittain, William D.G.
Authors
Alessia Santambrogio
Ben J. Murray
Lee T. Boulton
Dr Juan Aguilar Malavia j.a.aguilar@durham.ac.uk
Solution NMR Service Senior Manager
Dr Dmitry Yufit d.s.yufit@durham.ac.uk
Academic Visitor
Graham Sandford
Dr Will Brittain william.d.brittain@durham.ac.uk
Associate Professor
Abstract
Trifluoromethyl ynones derived from the refrigerant gas HFO-1234yf (2,3,3,3-tetrafluoropropene) react with nucleophiles via a Michael-type addition process and the allenolate intermediate formed reacts intramolecularly with a carbonyl group to form heterocyclic derivatives. Thus, reaction of 2-amino and 2-hydroxyl benzaldehyde or ketone substrates with trifluoromethyl ynone derivatives gives trifluoromethyl quinoline and chromene products by a one-pot tandem ring closing sequence, forming pharmaceutically relevant structures from an inexpensive starting material without the need for transition metals or column chromatography. The 2-trifluoromethylquinoline products also show unusual fluxional behaviour, which was explored through 2-D NMR and X-ray crystallographic studies.
Citation
Marsh, T. G., Santambrogio, A., Murray, B. J., Boulton, L. T., Aguilar, J. A., Yufit, D. S., …Brittain, W. D. (2023). HFO‐1234yf as a CF3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones. European Journal of Organic Chemistry, 26(11), Article e202300058. https://doi.org/10.1002/ejoc.202300058
Journal Article Type | Article |
---|---|
Acceptance Date | Jan 24, 2023 |
Online Publication Date | Feb 15, 2023 |
Publication Date | 2023-03 |
Deposit Date | Feb 24, 2023 |
Publicly Available Date | May 30, 2023 |
Journal | European Journal of Organic Chemistry |
Print ISSN | 1434-193X |
Electronic ISSN | 1099-0690 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
Volume | 26 |
Issue | 11 |
Article Number | e202300058 |
DOI | https://doi.org/10.1002/ejoc.202300058 |
Public URL | https://durham-repository.worktribe.com/output/1178501 |
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Copyright Statement
© 2023 The Authors. European Journal of Organic Chemistry 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.
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