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author:

Wu, Wei (Wu, Wei.) [1] | Wang, Junwen (Wang, Junwen.) [2] | Wang, Yukang (Wang, Yukang.) [3] | Huang, Yangjie (Huang, Yangjie.) [4] | Tan, Yingfei (Tan, Yingfei.) [5] | Weng, Zhiqiang (Weng, Zhiqiang.) [6]

Indexed by:

EI

Abstract:

A copper(I)-catalyzed interrupted click reaction in the presence of trifluoroacetic anhydride has been developed, wherein an N-trifluoroacetyl group is used to accelerate the ring-opening of the putative 5-copper(I) triazolide intermediate. Under the optimized reaction conditions, a broad range of azides and alkynes were found to participate in this transformation, thus affording 3-trifluoromethyl-substituted 1,2,4-triazinones in moderate to excellent yields. The reaction has proven to be compatible with a variety of electron-withdrawing and electron–donating groups, halogens, and nitrogen- and sulfur-containing heterocycles, as well as pharmaceutically relevant molecules. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keyword:

Catalysis Copper Copper compounds Cycloaddition Fluorine Reaction intermediates

Community:

  • [ 1 ] [Wu, Wei]State Key Laboratory of Photocatalysis on Energy and Environment College of Chemistry, Fuzhou University, Fuzhou; 350108, China
  • [ 2 ] [Wang, Junwen]State Key Laboratory of Photocatalysis on Energy and Environment College of Chemistry, Fuzhou University, Fuzhou; 350108, China
  • [ 3 ] [Wang, Yukang]State Key Laboratory of Photocatalysis on Energy and Environment College of Chemistry, Fuzhou University, Fuzhou; 350108, China
  • [ 4 ] [Huang, Yangjie]State Key Laboratory of Photocatalysis on Energy and Environment College of Chemistry, Fuzhou University, Fuzhou; 350108, China
  • [ 5 ] [Tan, Yingfei]State Key Laboratory of Photocatalysis on Energy and Environment College of Chemistry, Fuzhou University, Fuzhou; 350108, China
  • [ 6 ] [Weng, Zhiqiang]State Key Laboratory of Photocatalysis on Energy and Environment College of Chemistry, Fuzhou University, Fuzhou; 350108, China

Reprint 's Address:

  • [weng, zhiqiang]state key laboratory of photocatalysis on energy and environment college of chemistry, fuzhou university, fuzhou; 350108, china

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Source :

Angewandte Chemie - International Edition

ISSN: 1433-7851

Year: 2017

Issue: 35

Volume: 56

Page: 10476-10480

1 2 . 1 0 2

JCR@2017

1 6 . 1 0 0

JCR@2023

ESI HC Threshold:226

JCR Journal Grade:1

CAS Journal Grade:2

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count: 64

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 2

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