Photocatalytic Fluorosulfonylation/Fluorosulfonamidation of <i>N</i>-Homoallyl Aldehyde Hydrazones to Access FSO<sub>2</sub>-/FSO<sub>2</sub>N-Functionalized Tetrahydropyridazines

Sulfonyl/sulfamoyl fluoride and tetrahydropyridazine cores represent pivotal structural units in chemical and medicinal science. We herein disclose a photocatalytic strategy for the fluorosulfonylation/fluorosulfonamidation of <i>N</i>-homoallyl aldehyde hydrazones using FABI (1-fluorosulfonyl-2-arylbenzoimidazolium triflate salts) and NFSAP (<i>N</i>-fluorosulfamoylpyridinium salts), enabling efficient access to sulfonyl-/sulfamoyl-substituted tetrahydropyridazines. This protocol demonstrates excellent synthetic scalability and facilitates diverse postderivatization reactions, including SuFEx click reactions and elimination processes. Preliminary mechanistic studies reveal that the transformation proceeds via a fluorosulfonyl/fluorosulfonamidyl radical-mediated cascade cyclization pathway.

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Publication Details

Journal
Organic Letters
Published
2025-07-14
DOI
https://doi.org/10.1021/acs.orglett.5c02385
Citations
3
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
2.81
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Photocatalytic Fluorosulfonylation/Fluorosulfonamidation of N-Homoallyl Aldehyde Hydrazones to Access FSO2-/FSO2N-Functionalized Tetrahydropyridazines

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3 citations
Organic Letters
Sulfur-Based Synthesis Techniques
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article

Photocatalytic Fluorosulfonylation/Fluorosulfonamidation of N-Homoallyl Aldehyde Hydrazones to Access FSO2-/FSO2N-Functionalized Tetrahydropyridazines

Qi Lin, Wei Li, Yuan Lu, Yichen Dong, Lijin Wang, Yu-Xue Ma
article en
3 citations

Abstract

Sulfonyl/sulfamoyl fluoride and tetrahydropyridazine cores represent pivotal structural units in chemical and medicinal science. We herein disclose a photocatalytic strategy for the fluorosulfonylation/fluorosulfonamidation of <i>N</i>-homoallyl aldehyde hydrazones using FABI (1-fluorosulfonyl-2-arylbenzoimidazolium triflate salts) and NFSAP (<i>N</i>-fluorosulfamoylpyridinium salts), enabling efficient access to sulfonyl-/sulfamoyl-substituted tetrahydropyridazines. This protocol demonstrates excellent synthetic scalability and facilitates diverse postderivatization reactions, including SuFEx click reactions and elimination processes. Preliminary mechanistic studies reveal that the transformation proceeds via a fluorosulfonyl/fluorosulfonamidyl radical-mediated cascade cyclization pathway.

Organic LettersVol. 27(29)
Ministry of Education of the People's Republic of China (CN), Hebei University (CN)
Clean water and sanitation
Openalex Percentile: Top 10%
Sulfur-Based Synthesis Techniques
2.81
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Photocatalytic Fluorosulfonylation/Fluorosulfonamidation of <i>N</i>-Homoallyl Aldehyde Hydrazones to Access FSO<sub>2</sub>-/FSO<sub>2</sub>N-Functionalized Tetrahydropyridazines — Qi Lin, Wei Li, et al. · Organic Letters (2025) | TGRS Research Map | TGRS