posted on 2019-03-06, 20:03authored bySocrates
B. Munoz, Huong Dang, Xanath Ispizua-Rodriguez, Thomas Mathew, G. K. Surya Prakash
A fast and simple
method for deoxyfluorination of carboxylic acids
is presented. The protocol employs commodity chemicals (PPh3, NBS, fluoride), affording products in excellent yields under mild
conditions. Acyloxyphosphonium ion, the key reaction intermediate,
was identified by NMR spectroscopic methods. Brønsted acidic
conditions are essential for efficient C–F bond formation.
The protocol displays scalability, high functional group tolerance,
chemoselectivity, and easy purification of products. Deoxyfluorination
of active pharmaceutical ingredients was established.