SulfoxFluor-enabled deoxyazidation of alcohols with NaN<sub>3</sub>.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 35585073.
- Also identified by DOI 10.1038/s41467-022-30132-x and PMC identifier 9117260.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
Abstract
Direct deoxyazidation of alcohols with NaN<sub>3</sub> 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<sub>3</sub> 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.