Access to some C5-cyclised 2 pyrones and 2-pyridones via direct arylation; retention of chloride as a synthetic handle

Thumbnail Image
Files
3518.pdf(1.53 MB)
Accepted Version
ejoc201700980-sup-0001-SI1.pdf(1.36 MB)
Supplementary information
Date
2017-08-04
Authors
McGlacken, Gerard P.
Fairlamb, Ian
Prendergast, Aisling
Pardo, Leticia
Journal Title
Journal ISSN
Volume Title
Publisher
John Wiley & Sons, Ltd
Published Version
10.1002/ejoc.201700980
Research Projects
Organizational Units
Journal Issue
Abstract
The synthetic effort towards the functionalisation of C-H bonds on 2 pyrones and 2-pyridones has been funnelled by the preferential reactivity of the C-3 position. Herein, we report a direct arylation protocol for the intramolecular coupling of 2 pyrones and 2 pyridones, allowing access to a previously unavailable class of C-5 cyclised products with an unstudied biological profile. A C-Cl bond was retained at C-3 during the direct arylation process allowing further derivatisation at C-3, which we have demonstrated with a proof-of-principle Suzuki-Miyaura cross-coupling reaction.
Description
Keywords
C-H activation , Cross-coupling , Heterocycles , Palladium , Synthetic methods
Citation
McGlacken, G. P., Fairlamb, I., Prendergast, A. and Pardo, L. (2017) 'Access to some C5-cyclised 2 pyrones and 2-pyridones via direct arylation; retention of chloride as a synthetic handle', European Journal of Organic Chemistry, 2017(34), pp. 5119-5124. doi:10.1002/ejoc.201700980
URI
http://hdl.handle.net/10468/4685
Collections
Chemistry - Journal Articles
Copyright
© 2017, John Wiley & Sons Ltd. This is the peer reviewed version of the following article: McGlacken, G. P., Fairlamb, I., Prendergast, A. and Pardo, L. (2017) 'Access to some C5-cyclised 2 pyrones and 2-pyridones via direct arylation; retention of chloride as a synthetic handle', European Journal of Organic Chemistry, 2017(34), pp. 5119-5124, which has been published in final form at http://dx.doi.org/ 10.1002/ejoc.201700980. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.