Vishwakarma, Dharmendra S, Moses, John E (July 2024) Benzene‐1,3‐disulfonyl fluoride and Benzene‐1,3,5‐trisulfonyl fluoride: Low‐Cost, Stable, and Selective Reagents for SuFEx‐Driven Deoxyazidation. Advanced Synthesis and Catalysis. ISSN 1615-4150
Abstract
The development of synthetic methods for the synthesis of organic azides is highly important, given their critical role in advancing click chemistry over the last twenty years. We report a reagent‐economical, reliable, and scalable synthesis of alkyl azides from primary and secondary alcohols. This robust click method capitalizes on the synergistic interaction between Sulfur Fluoride Exchange (SuFEx) reagents – specifically, benzene‐1,3‐disulfonyl fluoride (BDSF) or benzene‐1,3,5‐trisulfonyl fluoride (BTSF) – and trimethylsilyl azide (TMSN3). The method offers procedural ease, accommodates a wide array of substrates, and enables late‐stage functionalization. Additionally, we demonstrate the protocol‘s adaptability by validating a straightforward one‐pot deoxyazidation‐CuAAC sequence for drug discovery applications.
| Item Type: | Paper |
|---|---|
| Subjects: | chemistry > techniques > click chemistry > Accelerated SuFEx Click Chemistry chemistry chemistry > techniques > click chemistry chemistry > techniques |
| CSHL Authors: | |
| Communities: | CSHL labs > Moses lab |
| SWORD Depositor: | CSHL Elements |
| Depositing User: | CSHL Elements |
| Date: | 23 July 2024 |
| Date Deposited: | 16 Sep 2024 13:42 |
| Last Modified: | 16 Sep 2024 13:42 |
| Related URLs: | |
| URI: | https://repository.cshl.edu/id/eprint/41664 |
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