Bachollet, S.P.J.T., Vivat, J.F., Cocker, D.C. et al. (2 more authors) (2014) Development of a Mild and Versatile Directed Cycloaddition Approach to Pyridines. Chemistry - A European Journal, 20 (40). 12889 - 12893. ISSN 0947-6539
Abstract
The aza-Diels–Alder cycloaddition of 1,2,4-triazines with alkynes offers a rapid and convenient method for the synthesis of highly substituted pyridines, but often requires harsh conditions and long reaction times. The present study offers a solution to these limitations by use of a temporary tether established by a Lewis acid–base complexation of in situ generated alkynylboranes and triazines bearing a Lewis basic donor. The cycloaddition reactions take place within 20 min at 40 °C and provide direct access to a broad range of pyridines with complete and predictable regiocontrol. The carbon[BOND]boron bond can be further functionalised by cross-coupling allowing further functionality to be introduced after cycloaddition.
Metadata
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Copyright, Publisher and Additional Information: | © 2014 The Author(s). This is an Open Access article distributed under the terms of the Creative Commons Attribution Licence (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. | ||||
Keywords: | boranes; cycloadditions; pyridine; regioselectivitv; triazines | ||||
Dates: |
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Institution: | The University of Sheffield | ||||
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) | ||||
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Depositing User: | Symplectic Sheffield | ||||
Date Deposited: | 03 Mar 2015 10:10 | ||||
Last Modified: | 03 Mar 2015 10:10 | ||||
Published Version: | http://dx.doi.org/10.1002/chem.201403916 | ||||
Status: | Published | ||||
Publisher: | John Wiley & Sons | ||||
Refereed: | Yes | ||||
Identification Number: | https://doi.org/10.1002/chem.201403916 |