Guo Junkai, Wang Xiu, Ni Chuanfa, Wan Xiaolong, Hu Jinbo
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032, China.
Nat Commun. 2022 May 18;13(1):2752. doi: 10.1038/s41467-022-30132-x.
Direct deoxyazidation of alcohols with NaN is a straightforward method for the synthesis of widely used alkyl azides in organic chemistry. However, known methods have some limitations such as high reaction temperatures and narrow substrate scope. Herein, a general and practical method for the preparation of alkyl azides from alcohols using NaN has been developed. N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor) plays an important role in this deoxyazidation process, which converts a broad range of alcohols into alkyl azides at room temperature. The power of this deoxyazidation protocol has been demonstrated by successful late-stage deoxyazidation of natural products and pharmaceutically relevant molecules.
用NaN对醇进行直接脱氧叠氮化是有机化学中合成广泛使用的烷基叠氮化物的一种直接方法。然而，已知方法存在一些局限性，如反应温度高和底物范围窄。在此，已开发出一种使用NaN从醇制备烷基叠氮化物的通用且实用的方法。N-对甲苯磺酰基-4-氯苯磺酰亚胺氟化物（SulfoxFluor）在该脱氧叠氮化过程中起着重要作用，它能在室温下将多种醇转化为烷基叠氮化物。天然产物和药学相关分子的成功后期脱氧叠氮化证明了这种脱氧叠氮化方法的有效性。
