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author:

Chen, Dengfeng (Chen, Dengfeng.) [1] | Nie, Xingliang (Nie, Xingliang.) [2] | Feng, Qingyuan (Feng, Qingyuan.) [3] | Zhang, Yingyin (Zhang, Yingyin.) [4] | Wang, Yiheng (Wang, Yiheng.) [5] | Wang, Qiuyue (Wang, Qiuyue.) [6] | Huang, Lin (Huang, Lin.) [7] | Huang, Shenlin (Huang, Shenlin.) [8] | Liao, Saihu (Liao, Saihu.) [9] (Scholars:廖赛虎)

Indexed by:

EI SCIE

Abstract:

Radical fluorosulfonylation is emerging as an appealing approach for the synthesis of sulfonyl fluorides, which have widespread applications in many fields, in particular in the context of chemical biology and drug development. Here, we report the first investigation of FSO2 radical generation under electrochemical conditions, and the establishment of a new and facile approach for the synthesis of beta-keto sulfonyl fluorides via oxo-fluorosulfonylation of alkynes with sulfuryl chlorofluoride as the radical precursor and air as the oxidant. This electrochemical protocol is amenable to access two different products (beta-keto sulfonyl fluorides or alpha-chloro-beta-keto sulfonyl fluorides) with the same reactants. The beta-keto sulfonyl fluoride products can be utilized as useful building blocks in the synthesis of various derivatives and heterocycles, including the first synthesis of an oxathiazole dioxide compound. Furthermore, some beta-keto sulfonyl fluorides and derivatives exhibited notably potent activities against Bursaphelenchus xylophilus and Colletotrichum gloeosporioides.

Keyword:

alkynes electrochemistry radical reactions SuFEx click chemistry sulfonyl fluorides

Community:

  • [ 1 ] [Chen, Dengfeng]Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Peoples R China
  • [ 2 ] [Feng, Qingyuan]Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Peoples R China
  • [ 3 ] [Zhang, Yingyin]Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Peoples R China
  • [ 4 ] [Huang, Shenlin]Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Peoples R China
  • [ 5 ] [Nie, Xingliang]Fuzhou Univ, Key Lab Mol Synth & Funct Discovery, Fujian Prov Univ, Coll Chem, Fuzhou 350108, Peoples R China
  • [ 6 ] [Liao, Saihu]Fuzhou Univ, Key Lab Mol Synth & Funct Discovery, Fujian Prov Univ, Coll Chem, Fuzhou 350108, Peoples R China
  • [ 7 ] [Wang, Yiheng]Nanjing Forestry Univ, Coinnovat Ctr Sustainable Forestry Southern China, Nanjing 210037, Peoples R China
  • [ 8 ] [Wang, Qiuyue]Nanjing Forestry Univ, Coinnovat Ctr Sustainable Forestry Southern China, Nanjing 210037, Peoples R China
  • [ 9 ] [Huang, Lin]Nanjing Forestry Univ, Coinnovat Ctr Sustainable Forestry Southern China, Nanjing 210037, Peoples R China
  • [ 10 ] [Liao, Saihu]Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

Reprint 's Address:

  • 廖赛虎

    [Huang, Shenlin]Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Peoples R China;;[Liao, Saihu]Fuzhou Univ, Key Lab Mol Synth & Funct Discovery, Fujian Prov Univ, Coll Chem, Fuzhou 350108, Peoples R China;;[Liao, Saihu]Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

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Source :

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

ISSN: 1433-7851

Year: 2021

Issue: 52

Volume: 60

Page: 27271-27276

1 6 . 8 2 3

JCR@2021

1 6 . 1 0 0

JCR@2023

ESI Discipline: CHEMISTRY;

ESI HC Threshold:117

JCR Journal Grade:1

CAS Journal Grade:2

Cited Count:

WoS CC Cited Count: 58

SCOPUS Cited Count: 59

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 1

Online/Total:141/10000789
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