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

Chen Zhu, Haifeng Chen, Huifeng Yue, Magnus Rueping

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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.
Original languageEnglish (US)
JournalNature Synthesis
StatePublished - Jun 22 2023

Bibliographical note

KAUST Repository Item: Exported on 2023-07-18
Acknowledged KAUST grant number(s): URF/1/4025
Acknowledgements: 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).


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