Cross-coupling of amide and amide derivatives to umbelliferone nonaflates: synthesis of coumarin derivatives and fluorescent materials
- Author(s)
- Hickey, SM; Nitschke, SO; Sweetman, MJ; Sumby, CJ; Brooks, DA; Plush, SE; Ashton, TD;
- Details
- Publication Year 2020,Volume 85,Issue #12,Page 7986-7999
- Journal Title
- Journal of Organic Chemistry
- Publication Type
- Journal Article
- Abstract
- The Buchwald–Hartwig cross-coupling reaction between 4-methylumbelliferone-derived nonaflates with amides, carbamates, and sulfonamides is described. A wide variety of N-substituted 7-amino coumarin analogues was prepared in good to excellent yields. The photophysical properties of aqueous-soluble derivatives were determined, and they displayed auxochrome-based variations. Gram-scale synthesis provided an acrylamide analogue, which was used to fabricate a fluorescent poly(2-hydroxylethyl methacrylate) (pHEMA) hydrogel that was resistant to leaching in ultrapure H2O. We envisage that our reported protocol to access 7-amino-4-methylcoumarin derivatives will find use toward the development of new fluorescent coumarin-based probes by researchers in the field.
- Publisher
- ACS
- Research Division(s)
- Chemical Biology
- Publisher's Version
- https://doi.org/10.1021/acs.joc.0c00813
- Terms of Use/Rights Notice
- Refer to copyright notice on published article.
Creation Date: 2020-08-05 10:22:52
Last Modified: 2020-08-05 10:31:26