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author:

Ye, M. (Ye, M..) [1] | Hou, M. (Hou, M..) [2] | Wang, Y. (Wang, Y..) [3] | Ma, X. (Ma, X..) [4] | Yang, K. (Yang, K..) [5] | Song, Q. (Song, Q..) [6]

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Abstract:

Alkynes are attractive synthons for organic chemistry. Despite the prevalence of transition-metal-catalyzed Sonogashira reactions, a transition-metal-free version of the arylation of terminal alkynes is elusive. Herein, we report an efficient transition-metal-free Sonogashira-type coupling reaction for the one-pot arylation of alkynes to construct C(sp)-C(sp2) bonds from a tetracoordinate boron intermediate with NIS as a mediator. With its high efficiency, wide substrate range, and good functional group tolerance, this method is further supported by the gram-scale synthesis and subsequent modification of complex molecules. © 2023 American Chemical Society.

Keyword:

Community:

  • [ 1 ] [Ye, M.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry at Fuzhou University, Fujian Province University, Fujian, Fuzhou, 350108, China
  • [ 2 ] [Hou, M.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry at Fuzhou University, Fujian Province University, Fujian, Fuzhou, 350108, China
  • [ 3 ] [Wang, Y.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry at Fuzhou University, Fujian Province University, Fujian, Fuzhou, 350108, China
  • [ 4 ] [Ma, X.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry at Fuzhou University, Fujian Province University, Fujian, Fuzhou, 350108, China
  • [ 5 ] [Yang, K.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry at Fuzhou University, Fujian Province University, Fujian, Fuzhou, 350108, China
  • [ 6 ] [Song, Q.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry at Fuzhou University, Fujian Province University, Fujian, Fuzhou, 350108, China
  • [ 7 ] [Song, Q.]School of Chemistry and Chemical Engineering, Henan Normal University, Henan, Xinxiang, 453007, China

Reprint 's Address:

  • [Song, Q.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian, China

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Source :

Organic Letters

ISSN: 1523-7060

Year: 2023

Issue: 10

Volume: 25

Page: 1787-1792

4 . 9

JCR@2023

4 . 9 0 0

JCR@2023

ESI HC Threshold:39

JCR Journal Grade:1

CAS Journal Grade:1

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count: 7

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 1

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