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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.

HFO‐1234yf as a CF3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones Thumbnail


Authors

Thomas G.F. Marsh

Alessia Santambrogio

Ben J. Murray

Lee T. Boulton

Graham Sandford



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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Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/

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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