State Key Laboratory of Elemento-Organic Chemistry, The Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, P. R. China.
Chemistry. 2022 May 11;28(27):e202200272. doi: 10.1002/chem.202200272. Epub 2022 Apr 1.
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 2 pathway involving PPh 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.
开发方便的有机叠氮化物合成新方法是非常可取的。在此，我们报告了一种通过 S 2 途径涉及 PPh 和三功能苯并碘唑啉酮基高价叠氮碘（III）试剂的醇去羟叠氮化的实用方法，该试剂作为亲电中心、叠氮源和碱。这种温和、选择性化学的方法可用于结构复杂的醇的后期叠氮化，以及抗癫痫药物鲁非酰胺的新合成途径。还通过实验和计算研究了反应机理。
