Premium
Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water
Author(s) -
Bora Pranjal P.,
Bihani Manisha,
Plummer Scott,
Gallou Fabrice,
Handa Sachin
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201900316
Subject(s) - micelle , solubility , chemistry , fluorine , substrate (aquarium) , selectivity , amphiphile , chemical engineering , combinatorial chemistry , photochemistry , organic chemistry , aqueous solution , catalysis , polymer , copolymer , oceanography , engineering , geology
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.