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We report a reagent\u2010economical, 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 \u2013 specifically, benzene\u20101,3\u2010disulfonyl fluoride (BDSF) or benzene\u20101,3,5\u2010trisulfonyl fluoride (BTSF) \u2013 and trimethylsilyl azide (TMSN\n                    <jats:sub>3<\/jats:sub>\n                    ). The method offers procedural ease, accommodates a wide array of substrates, and enables late\u2010stage functionalization. Additionally, we demonstrate the protocol\u2018s adaptability by validating a straightforward one\u2010pot deoxyazidation\u2010CuAAC sequence for drug discovery applications.\n                  <\/jats:p>","DOI":"10.1002\/adsc.202400680","type":"journal-article","created":{"date-parts":[[2024,7,23]],"date-time":"2024-07-23T16:30:24Z","timestamp":1721752224000},"page":"4470-4477","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Benzene\u20101,3\u2010disulfonyl fluoride and Benzene\u20101,3,5\u2010trisulfonyl fluoride: Low\u2010Cost, Stable, and Selective Reagents for SuFEx\u2010Driven Deoxyazidation"],"prefix":"10.1002","volume":"366","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3298-0600","authenticated-orcid":false,"given":"Dharmendra S.","family":"Vishwakarma","sequence":"first","affiliation":[{"name":"Cancer Center Cold Spring Harbor Laboratory  1 Bungtown Road Cold Spring Harbor NY 11724 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2162-3234","authenticated-orcid":false,"given":"John E.","family":"Moses","sequence":"additional","affiliation":[{"name":"Cancer Center Cold Spring Harbor Laboratory  1 Bungtown Road Cold Spring Harbor NY 11724 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,9,12]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo011148j"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9PY00510B"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.1c00564"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11095-008-9616-1"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1080\/17460441.2019.1614910"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/med.20107"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.201302847"},{"key":"e_1_2_6_11_1","unstructured":"While there was an air of skepticism initially partly because of concerns regarding azide stability and safety it was more a cautious assessment than a barrier. This notion captured by Sharpless's coined term \u201cazidophobia\u201d referring to an overcautious attitude towards azides that while notable did not significantly overshadow their practical utility."},{"key":"e_1_2_6_12_1","unstructured":"University of California Santa Barbara \u201cLaboratory safety fact sheet #26: synthesizing purifying and handling organic azides\u201d.https:\/\/www.ehs.ucsb.edu\/sites\/default\/files\/docs\/ls\/factsheets\/Azides_FS26.pdf."},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-019-1589-1"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja106712z"},{"key":"e_1_2_6_15_1","unstructured":"\u00a0"},{"key":"e_1_2_6_16_2","unstructured":"Results were obtained from a non-exhaustive search of the academic and patent literature via the Reaxys web-based tool. A \u201cquick search\u201d was conducted using the \u201cstructure drawer function\u201d whereby an azide functional group (\u2212N3) was formed as a product of a reaction. Independent searches for the synthesis of aliphatic and aromatic azides were conducted. Results were exported to Microsoft Excel combined and grouped by year. Values for the last 123\u2005years (1900\u20132023) are presented in a bar chart format;"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.3390\/catal10101173"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c01124"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic50026a027"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01284a050"},{"key":"e_1_2_6_21_1","unstructured":"R.\u2005J Shozda US. Patent 3418088A1968(Chem. 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Additionally the presence of silicon would facilitate S\u2212F to S\u2212O bond exchange driven by the formation of a strong Si\u2212F bond. This approach is aimed at enhancing the efficiency and practicality of deoxyazidation reactions."},{"key":"e_1_2_6_59_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jasms.2005.01.014"},{"key":"e_1_2_6_60_1","doi-asserted-by":"publisher","DOI":"10.1155\/2014\/454503"},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c01016"},{"key":"e_1_2_6_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00253a040"},{"key":"e_1_2_6_63_1","unstructured":"The deoxyazidation reaction of quinine (1\u2009ai) proceeded with stereochemical inversion as determined upon comparison to literature NMR data. For more information refer to Ref.\u2005[57] and Supporting Information."},{"key":"e_1_2_6_64_1","doi-asserted-by":"publisher","DOI":"10.1016\/0957-4166(95)00215-B"},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.102939"},{"key":"e_1_2_6_66_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100791"},{"key":"e_1_2_6_67_1","doi-asserted-by":"publisher","DOI":"10.6118\/jmm.2017.23.2.79"},{"key":"e_1_2_6_68_1","unstructured":"SuFEx reactions involving silyl ethers are well-documented for their ability to enhance the reaction rate. 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