Amer Alhaj Zen
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.
Jonathan W. Aylott
Weng C. Chan
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|
|Peer Reviewed||Peer Reviewed|
|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|
|Keywords||Coumarin, Suzuki cross-coupling, Arylboronic MIDA ester, Fluorescence|
|Copyright Statement||Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nd/4.0|
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nd/4.0