Plummer, Scott and Gallou, Fabrice (2019) Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water. ChemSusChem, 12. pp. 3037-3042. ISSN 1864-564X; 1864-5631

Abstract

Using an approach which allows site-specific solubility of substrate and fluorine source in the micelle, highly-selective direct monofluorination of indoles and arenes was developed. This approach is highly selective on a broad range of substrates withexcellent functional group tolerance. Differences in binding constant and solubility of indoles and arenes in the micelle allowed the finetuning of selectivity. Control experiments suggested a radical pathway and provided insight into the role of micelles of environmentally benign amphiphile PS-750-M. DLS experiments strongly indicated the sitespecific solubility of the substrate and fluorine source. The methodology was successfully adapted to gram-scale, and the E factor established from a recycle study indicates that the process is environmentally responsible and sustainable.

Item Type:	Article
Date Deposited:	10 Dec 2019 00:45
Last Modified:	10 Dec 2019 00:45
URI:	https://oak.novartis.com/id/eprint/38895