An appraisal of the Suzuki cross-coupling reaction for the synthesis of novel fluorescent coumarin derivatives
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 e...
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| Format: | Article |
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Elsevier
2014
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| Online Access: | https://eprints.nottingham.ac.uk/37547/ |
| _version_ | 1848795482219872256 |
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| author | Alhaj Zen, Amer Aylott, Jonathan W. Chan, Weng C. |
| author_facet | Alhaj Zen, Amer Aylott, Jonathan W. Chan, Weng C. |
| author_sort | Alhaj Zen, Amer |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T19:32:47Z |
| format | Article |
| id | nottingham-37547 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:32:47Z |
| publishDate | 2014 |
| publisher | Elsevier |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-375472020-05-04T16:52:49Z https://eprints.nottingham.ac.uk/37547/ 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. 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. Elsevier 2014-10-01 Article PeerReviewed Alhaj Zen, Amer, Aylott, Jonathan W. and Chan, Weng C. (2014) An appraisal of the Suzuki cross-coupling reaction for the synthesis of novel fluorescent coumarin derivatives. Tetrahedron Letters, 55 (40). pp. 5521-5524. ISSN 0040-4039 Coumarin Suzuki cross-coupling Arylboronic MIDA ester Fluorescence http://www.sciencedirect.com/science/article/pii/S0040403914013926 doi:10.1016/j.tetlet.2014.08.058 doi:10.1016/j.tetlet.2014.08.058 |
| spellingShingle | Coumarin Suzuki cross-coupling Arylboronic MIDA ester Fluorescence Alhaj Zen, Amer Aylott, Jonathan W. Chan, Weng C. An appraisal of the Suzuki cross-coupling reaction for the synthesis of novel fluorescent coumarin derivatives |
| title | An appraisal of the Suzuki cross-coupling reaction for the synthesis of novel fluorescent coumarin derivatives |
| title_full | An appraisal of the Suzuki cross-coupling reaction for the synthesis of novel fluorescent coumarin derivatives |
| title_fullStr | An appraisal of the Suzuki cross-coupling reaction for the synthesis of novel fluorescent coumarin derivatives |
| title_full_unstemmed | An appraisal of the Suzuki cross-coupling reaction for the synthesis of novel fluorescent coumarin derivatives |
| title_short | An appraisal of the Suzuki cross-coupling reaction for the synthesis of novel fluorescent coumarin derivatives |
| title_sort | appraisal of the suzuki cross-coupling reaction for the synthesis of novel fluorescent coumarin derivatives |
| topic | Coumarin Suzuki cross-coupling Arylboronic MIDA ester Fluorescence |
| url | https://eprints.nottingham.ac.uk/37547/ https://eprints.nottingham.ac.uk/37547/ https://eprints.nottingham.ac.uk/37547/ |