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author:

Bao, J. (Bao, J..) [1] | Wei, R. (Wei, R..) [2] | Li, Y. (Li, Y..) [3] | Bao, H. (Bao, H..) [4]

Indexed by:

Scopus

Abstract:

Ionic 1,4-difunctionalization of 1,3-enynes has often been conducted with strong nucleophiles or 1,3-enynes that are activated by an electron-withdrawing group. In this work, a palladium-catalyzed three-component ionic 1,4-carboarylation of 1,3-enynes is reported with arylated 1,3-enynes as the substrates. This method can afford various tetrasubstituted allenes with different functionalities. The palladium salt might play a key dual role in the reaction: as the catalyst to catalyze the cross-coupling reaction and as a Lewis acid to facilitate the nucleophilic attack. The synthetic value of this method is demonstrated by the further cyclization, decoration, and hydrolysis of the allene products. © 2022 Georg Thieme Verlag. All rights reserved.

Keyword:

1,3-enynes 1,4-difunctionalization ionic reaction palladium tetrasubstituted allenes

Community:

  • [ 1 ] [Bao, J.]College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 2 ] [Bao, J.]Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, China
  • [ 3 ] [Wei, R.]College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 4 ] [Wei, R.]Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, China
  • [ 5 ] [Li, Y.]Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, China
  • [ 6 ] [Bao, H.]Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, China
  • [ 7 ] [Bao, H.]University of Chinese Academy of Sciences, Beijing, 100049, China

Reprint 's Address:

  • [Li, Y.]Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, China

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Source :

Synthesis (Germany)

ISSN: 0039-7881

Year: 2022

Issue: 16

Volume: 54

Page: 3631-3641

2 . 6

JCR@2022

2 . 2 0 0

JCR@2023

ESI HC Threshold:74

JCR Journal Grade:2

CAS Journal Grade:3

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count:

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 0

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