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An appraisal of the Suzuki cross-coupling reaction for the synthesis of novel fluorescent coumarin derivatives

Alhaj Zen, Amer; Aylott, Jonathan W.; Chan, Weng C.

Authors

Amer Alhaj Zen

Jonathan W. Aylott

Weng C. Chan



Abstract

We report the chemical design and development of 3-aryl-substituted 7-alkoxy-4-methylcoumarins with enhanced fluorogenic properties. The 3-aryl substituents are installed via an optimized Suzuki–Miyaura cross-coupling (SMC) reaction between a 7-alkoxy-3-bromo-4-methylcoumarin and aryl boronic MIDA esters using Pd(OAc)2/XPhos in a catalytic system with K2CO3 in aqueous THF. Under these conditions, an exocyclic ester functionality is found to be unaffected. Subsequent saponification revealed a carboxylic acid functionality that is suitable for conjugation reactions. Evaluation of their fluorescence properties indicated that the installed 3-heteroaryl substituent, particularly benzofuran-2-yl, resulted in a significant red shift of both the excitation and emission wavelengths.

Citation

Alhaj Zen, A., Aylott, J. W., & Chan, W. C. (2014). An appraisal of the Suzuki cross-coupling reaction for the synthesis of novel fluorescent coumarin derivatives. Tetrahedron Letters, 55(40), https://doi.org/10.1016/j.tetlet.2014.08.058

Journal Article Type Article
Acceptance Date Aug 13, 2014
Online Publication Date Aug 19, 2014
Publication Date Oct 1, 2014
Deposit Date Oct 13, 2016
Publicly Available Date Oct 13, 2016
Journal Tetrahedron Letters
Print ISSN 0040-4039
Electronic ISSN 0040-4039
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 55
Issue 40
DOI https://doi.org/10.1016/j.tetlet.2014.08.058
Keywords Coumarin, Suzuki cross-coupling, Arylboronic MIDA ester, Fluorescence
Public URL http://eprints.nottingham.ac.uk/id/eprint/37547
Publisher URL http://www.sciencedirect.com/science/article/pii/S0040403914013926
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nd/4.0

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nd/4.0





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