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author:

Zhu, Chen (Zhu, Chen.) [1] | Chen, Haifeng (Chen, Haifeng.) [2] | Yue, Huifeng (Yue, Huifeng.) [3] (Scholars:岳会锋) | Rueping, Magnus (Rueping, Magnus.) [4]

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ESCI

Abstract:

The development of general and efficient strategies for the construction of allenes is important due to their wide applications. Although few protocols have been developed via the 1,4-difunctionalization of 1,3-enynes under thermal or photoredox conditions, the mild and robust methodology for dicarbofunctionalization and hydroalkylation remains unexplored. In the present study, we report an electrochemical multicomponent protocol for the chemo- and regioselective difunctionalization of 1,3-enynes. In particular, 1,4-arylalkylation and unsymmetrical dialkylation have been realized via electro- and nickel dual catalysis using graphite/nickel foam and zinc/nickel foam as electrodes, respectively. The use of a Zn/reticulated vitreous carbon electrode led to efficient 1,4-hydro(deutero)alkylation in the absence of a metal catalyst. A wide range of structurally diverse tri- and tetra-substituted allenes were easily prepared with good efficiency and excellent regioselectivity under mild reaction conditions. Notably, a series of natural product- and drug-derived substrates could undergo late-stage functionalization to generate the corresponding complex allenes. The synthesis of allenes through 1,4-difunctionalization of 1,3-enynes typically requires preformed organometallic species, high temperature or specific alkyl radical precursors. Now an electrochemical multicomponent protocol for the chemo- and regioselective 1,4-difunctionalization of 1,3-enynes is reported, which uses alkyl bromides with aryl bromides, alkyl bromides or H2O/D2O as reagents for 1,4-difunctionalization.

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Community:

  • [ 1 ] [Zhu, Chen]King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Thuwal, Saudi Arabia
  • [ 2 ] [Chen, Haifeng]King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Thuwal, Saudi Arabia
  • [ 3 ] [Yue, Huifeng]King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Thuwal, Saudi Arabia
  • [ 4 ] [Rueping, Magnus]King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Thuwal, Saudi Arabia
  • [ 5 ] [Zhu, Chen]Eastern Inst Technol, Eastern Inst Adv Study, Ningbo, Peoples R China
  • [ 6 ] [Yue, Huifeng]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou, Peoples R China

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Source :

NATURE SYNTHESIS

ISSN: 2731-0582

Year: 2023

Issue: 11

Volume: 2

Page: 1068-1081

1 7 . 5

JCR@2023

1 7 . 5 0 0

JCR@2023

JCR Journal Grade:1

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count: 18

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 1

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