biostudies-literatureGuo JNational Natural Science Foundation of ChinaNational Natural Science Foundation of China (National Science Foundation of China)2752https://www.ebi.ac.uk/biostudies/studies/S-EPMC9117260biostudies-literatureUnknown13(1)Direct deoxyazidation of alcohols with NaN₃ 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 NaN₃ 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.Nature communicationsSulfoxFluor-enabled deoxyazidation of alcohols with NaN₃.PMC911726021632009Guo JHu JWang XNi CWan XfalseSulfoxFluor-enabled deoxyazidation of alcohols with NaN₃.Direct deoxyazidation of alcohols with NaN₃ 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 NaN₃ 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.2022-01-01T00:00:00Z2022 May2025-04-18T22:59:51.729Z2024-11-15T20:40:00.431ZS-EPMC91172603558507310.1038/s41467-022-30132-x