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author:

Wang, Peng (Wang, Peng.) [1] | Zhang, Honghai (Zhang, Honghai.) [2] | Zhao, Mingqi (Zhao, Mingqi.) [3] | Ji, Shuangshuang (Ji, Shuangshuang.) [4] | Lin, Lu (Lin, Lu.) [5] | Yang, Na (Yang, Na.) [6] | Nie, Xingliang (Nie, Xingliang.) [7] | Song, Jinshuai (Song, Jinshuai.) [8] | Liao, Saihu (Liao, Saihu.) [9] (Scholars:廖赛虎)

Indexed by:

EI Scopus SCIE

Abstract:

Recently, radical fluorosulfonylation is emerging as an appealing approach for the synthesis of sulfonyl fluorides, which are highly in demand in various disciplines, particularly in chemical biology and drug discovery. Here, we report the first establishment of radical hydro-fluorosulfonylation of alkenes, which is enabled by using 1-fluorosulfonyl 2-aryl benzoimidazolium (FABI) as an effective redox-active radical precursor. This method provides a new and facile approach for the synthesis of aliphatic sulfonyl fluorides from unactivated alkenes, and can be further applied to the late-stage modifications of natural products and peptides, as well as ligation of drugs in combination with click chemistry. Remarkably, this system could enable the radical hydro-fluorosulfonylation of alkynes, affording valuable alkenylsulfonyl fluoride products with a rare, high Z-selectivity, which are normally less stable and more challenging to synthesize in comparison with the E-configured products.

Keyword:

Alkenes Hydro-Fluorosulfonylation Organocatalysis Radical Reactions SuFEx

Community:

  • [ 1 ] [Wang, Peng]Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fujian Prov Univ,Key Lab Mol Synth & Funct Discov, Fuzhou 350108, Peoples R China
  • [ 2 ] [Zhang, Honghai]Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fujian Prov Univ,Key Lab Mol Synth & Funct Discov, Fuzhou 350108, Peoples R China
  • [ 3 ] [Lin, Lu]Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fujian Prov Univ,Key Lab Mol Synth & Funct Discov, Fuzhou 350108, Peoples R China
  • [ 4 ] [Yang, Na]Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fujian Prov Univ,Key Lab Mol Synth & Funct Discov, Fuzhou 350108, Peoples R China
  • [ 5 ] [Nie, Xingliang]Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fujian Prov Univ,Key Lab Mol Synth & Funct Discov, Fuzhou 350108, Peoples R China
  • [ 6 ] [Liao, Saihu]Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fujian Prov Univ,Key Lab Mol Synth & Funct Discov, Fuzhou 350108, Peoples R China
  • [ 7 ] [Zhao, Mingqi]Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China
  • [ 8 ] [Ji, Shuangshuang]Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China
  • [ 9 ] [Song, Jinshuai]Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China
  • [ 10 ] [Liao, Saihu]Beijing Natl Lab Mol Sci BNLMS, Beijing 100190, Peoples R China

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Source :

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

ISSN: 1433-7851

Year: 2022

Issue: 39

Volume: 61

1 6 . 6

JCR@2022

1 6 . 1 0 0

JCR@2023

ESI Discipline: CHEMISTRY;

ESI HC Threshold:74

JCR Journal Grade:1

CAS Journal Grade:1

Cited Count:

WoS CC Cited Count: 44

SCOPUS Cited Count: 43

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 3

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