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
Item Type: | Article |
---|---|
Authors/Creators: |
|
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: |
|
Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Funding Information: | Funder Grant number EPSRC EP/H005854/1 |
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: | 10.1002/chem.201403916 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:83927 |