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author:

Lin, B. (Lin, B..) [1] | Wu, W. (Wu, W..) [2] | Weng, Z. (Weng, Z..) [3]

Indexed by:

Scopus

Abstract:

A Cu-catalyzed interrupted click reaction for the synthesis of 3-perfluoroalkyl-substituted 1,2,4-triazinones is developed. The reaction between the terminal alkynes with azides and pentafluoropropionic or heptafluorobutyric anhydride proceeds smoothly to afford the corresponding pentafluoroethylated or heptafluoropropyled products in good yields. This protocol is applicable to various types of substrates including arylacetylenes and aliphatic azides having electron-rich and electron-deficient groups. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 3-perfluoroalkyl-substituted 1,2,4-triazinones. Some of the title compounds showed fungicidal activity against cucumber downy mildew (CDM). © 2019 Elsevier Ltd

Keyword:

Click chemistry; Copper; Fluorine; Perfluoroalkylation; Triazinones

Community:

  • [ 1 ] [Lin, B.]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 2 ] [Wu, W.]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 3 ] [Weng, Z.]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 4 ] [Weng, Z.]State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China

Reprint 's Address:

  • [Weng, Z.]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou UniversityChina

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Source :

Tetrahedron

ISSN: 0040-4020

Year: 2019

Issue: 19

Volume: 75

Page: 2843-2847

2 . 2 3 3

JCR@2019

2 . 1 0 0

JCR@2023

ESI HC Threshold:184

JCR Journal Grade:2

CAS Journal Grade:3

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count: 15

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 0

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