Late‐Stage Dehydroxyazidation of Alcohols Promoted by Trifunctional Hypervalent Azido‐Iodine(III) Reagents
Xiaoguang Yang, Feng‐Huan Du, Junjie Li, Chi Zhang
Abstract
Abstract The 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. This mild, chemoselective method was used for late‐stage azidation of structurally complex alcohols, as well as for a new synthetic route to the antiepileptic drug rufinamide. The reaction mechanism was also investigated both experimentally and computationally.
Topics & Concepts
Hypervalent moleculeReagentElectrophileIodineChemistryCombinatorial chemistryOrganic synthesisOrganic chemistryCatalysisSynthesis and Catalytic ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods