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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.

Journal Article Type Article
Publication Date Oct 1, 2014
Journal Tetrahedron Letters
Print ISSN 0040-4039
Electronic ISSN 0040-4039
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 55
Issue 40
APA6 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), doi:10.1016/j.tetlet.2014.08.058
DOI https://doi.org/10.1016/j.tetlet.2014.08.058
Keywords Coumarin, Suzuki cross-coupling, Arylboronic MIDA ester, Fluorescence
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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