Late-Stage Dehydroxyazidation of Alcohols Promoted by Trifunctional Hypervalent Azido-Iodine(III) Reagents

Chemistry. 2022 Mar 14. doi: 10.1002/chem.202200272. Online ahead of print.ABSTRACTThe development of convenient new methods for the synthesis of organic azides is highly desirable. Herein, we report a practical method for dehydroxyazidation of alcohols via an S N 2 pathway involving PPh 3 and trifunctional benziodazolone-based hypervalent azido-iodine(III) reagents, which function as an electrophilic center, an azido source, and a base. We successfully used this mild, chemoselective method for late-stage azidation of structurally complex alcohols, as well as for a new synthetic route to the antiepileptic drug rufinamide. We also investigated the reaction mechanism both experimentally and computationally.PMID:35286772 | DOI:10.1002/chem.202200272

Source: Chemistry - March 14, 2022 Category: Chemistry Authors: Xiao-Guang Yang Feng-Huan Du Jun-Jie Li Chi Zhang Source Type: research