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author：

Wang, P. (Wang, P..) [1] | Lin, L. (Lin, L..) [2] | Huang, Y. (Huang, Y..) [3] | Zhang, H. (Zhang, H..) [4] | Liao, S. (Liao, S..) [5]

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Scopus

Abstract：

Recently,　the　introduction　of　fluorosulfonyl　(−SO2F)　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.,　and　a　metal-free　protocol　is　also　viable　by　using　organic　photocatalysts.　Further,　FSAP　can　also　be　applied　to　the　radical　functionalization　of　alkenes　via　1,2-difunctionalization,　radical　distal　migration,　tandem　radical-polar　crossover　reactions,　etc.　In　addition,　a　formal　C−H　methylamination　of　(hetero)arenes　by　combining　this　radical　C−H　fluorosulfonamidation　with　subsequent　hydrolysis　as　well　as　product　derivatization　are　also　demonstrated.　©　2024　Wiley-VCH　GmbH.

Keyword：

N-Centered Radicals Photocatalysis Radical Reactions SuFEx Sulfamoyl Fluorides

Community：

  • [ 1 ] [Wang P.]Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 2 ] [Wang P.]Key Laboratory of Green and Precise Synthetic Chemistry and Application, Ministry of Education, College of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000, China
  • [ 3 ] [Lin L.]Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 4 ] [Lin L.]State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China
  • [ 5 ] [Huang Y.]Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 6 ] [Huang Y.]State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China
  • [ 7 ] [Zhang H.]Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 8 ] [Zhang H.]State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China
  • [ 9 ] [Liao S.]Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 10 ] [Liao S.]State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China

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Source ：

Angewandte Chemie - International Edition

ISSN： 1433-7851

Year： 2024

Issue： 34

Volume： 63

1 6 . 1 0 0

JCR@2023

Cited Count：

WoS CC Cited Count：

SCOPUS Cited Count： 2

ESI Highly Cited Papers on the List： 0 Unfold All

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30 Days PV： 0

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