Photocatalytic Radical Azido/Fluorosulfonylation of Unactivated Alkenes: Accessing Hubs Bridging CuAAC and SuFEx Click Chemistry
Herein, we describe the successful development of an azido-fluorosulfonylation reaction of alkenes under photoredox catalysis, which could allow the installation of the two "clickable" groups, -N<sub>3</sub> and -SO<sub>2</sub>F, on a C-C double bond, with TMSN<sub>3</sub> as the azide source. The utilization of the difunctionalization products is also demonstrated in the construction of a library of 1,2,3-triazolesulfonyl fluoride compounds as well as drug molecule ligation by merging copper-catalyzed azide-alkyne cycloaddition (CuAAC) and sulfur(VI) fluoride exchange (SuFEx), the two generations of click reactions. Mechanistic studies suggest a radical fluorosulfonylation/azidation mechanism and unveil FSO<sub>2</sub>N<sub>3</sub> as a new and potential fluorosulfonyl radical precursor.
Authors
- Rongbiao Wei (ORCID: https://orcid.org/0009-0002-7221-1045)
- Lu Lin
- Saihu Liao (ORCID: https://orcid.org/0000-0002-0251-8757)
- Guanhua Pei
- Honghai Zhang (ORCID: https://orcid.org/0000-0001-9576-4035)
- Peng Wang (ORCID: https://orcid.org/0009-0002-4416-6339)
Institutions
- Xiamen University (CN)
- Chemical Synthesis Lab (SG)
- Fuzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-28
- DOI
- https://doi.org/10.1021/acs.orglett.5c00426
- Citations
- 5
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- National Natural Science Foundation of China
- Fuzhou University
- Xiamen University