Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water. Issue 13 (26th March 2019)

• Record Type: Journal Article
• Authors: Bora, Pranjal P.; Bihani, Manisha; Plummer, Scott; Gallou, Fabrice; Handa, Sachin
• Is Part Of: ChemSusChem. Volume 12:Issue 13(2019)
• Page Start: 3037
• Page End: 3042
• Publication Date: 2019-03-26
• Subjects: E-factor -- fluorination -- green chemistry -- micelles -- sustainability; Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.201900316
• Languages: English
• ISSNs: 1864-5631

Abstract

Abstract: Highly selective direct monofluorination of indoles and arenes was developed through an approach that allows site‐specific solubility of substrate and fluorine source in the micelle. This approach was highly selective for a broad range of substrates with excellent functional group tolerance. Differences in binding constant and solubility of indoles and arenes in the micelle allowed the fine‐tuning of selectivity. Control experiments suggested a radical pathway and provided insight into the role of micelles of the environmentally benign amphiphile PS‐750‐M. Dynamic light scattering experiments strongly indicated the site‐specific solubility of the substrate and fluorine source. The methodology was successfully adapted to gram scale, and the E‐factor established from a recycle study indicated that the process is environmentally responsible and sustainable. Abstract : Micelles make the difference : Highly selective direct monofluorination of indoles and arenes is developed through an approach that allows site‐specific solubility of substrate and fluorine source in the micelle. This approach is suitable for a broad range of substrates with excellent functional group tolerance. Differences in binding constant and solubility of indoles and arenes in the micelle allow the fine‐tuning of selectivity.