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author:

Zhu, C. (Zhu, C..) [1] | Chen, H. (Chen, H..) [2] | Yue, H. (Yue, H..) [3] (Scholars:岳会锋) | Rueping, M. (Rueping, M..) [4]

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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. [Figure not available: see fulltext.]. © 2023, The Author(s), under exclusive licence to Springer Nature Limited.

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  • [ 1 ] [Zhu C.]KAUST Catalysis Center, King Abdullah University of Science and Technology, Thuwal, Saudi Arabia
  • [ 2 ] [Zhu C.]Eastern Institute for Advanced Study, Eastern Institute of Technology, Ningbo, China
  • [ 3 ] [Chen H.]KAUST Catalysis Center, King Abdullah University of Science and Technology, Thuwal, Saudi Arabia
  • [ 4 ] [Yue H.]KAUST Catalysis Center, King Abdullah University of Science and Technology, Thuwal, Saudi Arabia
  • [ 5 ] [Yue H.]Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou, China
  • [ 6 ] [Rueping M.]KAUST Catalysis Center, King Abdullah University of Science and Technology, Thuwal, Saudi Arabia

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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: 0

SCOPUS Cited Count: 10

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 1

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