Sulfamoyl fluorides, as a crucial building block of SuFEx, have garnered extensive research interest due to their unique properties. However, the direct radical fluorosulfonamidation process for the synthesis of sulfamoyl fluorides has been overlooked. We herein disclosed a practical procedure for constructing a redox-active fluorosulfonamide radical reagent named fluorosulfonyl--pyridinium tetrafluoroborate (PNSF) from SOF. These reagents can facilitate a range of reactions, including the -(fluorosulfonyl) sulfonamidation of (hetero)arenes, sequential radical stereoselective fluorosulfonamidation, and 1,2-difunctionalization of alkenes.
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Pyridinium-Based Fluorosulfonamide Reagents Enabled Photoredox-Catalyzed Radical Fluorosulfonamidation.
Org Lett
August 2024
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Collaborative Innovation Center of Advanced Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
Sulfamoyl fluorides, as a crucial building block of SuFEx, have garnered extensive research interest due to their unique properties. However, the direct radical fluorosulfonamidation process for the synthesis of sulfamoyl fluorides has been overlooked. We herein disclosed a practical procedure for constructing a redox-active fluorosulfonamide radical reagent named fluorosulfonyl--pyridinium tetrafluoroborate (PNSF) from SOF.
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Angew Chem Int Ed Engl
August 2024
Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou, 350108, China.
Recently, the introduction of fluorosulfonyl (-SOF) groups have attracted considerable research interests, as this moiety could often afford enhanced activities and new functions in the context of chemical biology and drug discovery. Herein, we report the design and synthesis of 1-fluorosulfamoyl-pyridinium (FSAP) salts, which could serve as an effective photoredox-active precursor to fluorosulfamoyl radicals and enable the direct radical C-H fluorosulfonamidation of a variety of (hetero)arenes. This method features mild conditions, visible light, broad substrate scope, good group tolerance, etc.
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