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

作者：Xiaoguang Yang, Feng‐Huan Du, Junjie Li, Chi Zhang · 发表于：Chemistry - A European Journal · 年份：2022 · DOI：10.1002/chem.202200272 · 被引用次数：24 · 研究领域：Synthesis and Catalytic Reactions、Oxidative Organic Chemistry Reactions、Catalytic C–H Functionalization Methods

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.