Electrochemical chemo- and regioselective arylalkylation, dialkylation and hydro(deutero)alkylation of 1,3-enynes

Chen Zhu, Haifeng Chen, Huifeng Yue*, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

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.].

Original languageEnglish (US)
Pages (from-to)1068-1081
Number of pages14
JournalNature Synthesis
Volume2
Issue number11
DOIs
StateAccepted/In press - 2023

Bibliographical note

Funding Information:
This work was financially supported by the King Abdullah University of Science and Technology (KAUST) and the Saudi Arabia, Office of Sponsored Research (URF/1/4025). C.Z. acknowledges the KAUST Supercomputing Laboratory for providing computational resources from the supercomputer Shaheen II (k1284).

Publisher Copyright:
© 2023, The Author(s), under exclusive licence to Springer Nature Limited.

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry

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