Group 14 Elements Hetero-Difunctionalizations via Nickel-Catalyzed Electroreductive Cross-Coupling

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations


The difunctionalization of unsaturated bonds plays a vital role in the enrichment of molecular complexity. While various catalytic methods for alkene and alkyne difunctionalization have been developed in recent years, hetero-functionalization the introduction of two different atoms has been less explored. This is mainly due to the challenges associated with achieving high chemo-, regio-, and stereoselectivity, especially when adding two similar atoms from the same group across unsaturated bonds. In this study, we describe a nickel-catalyzed, three-component reductive protocol for group 14 element hetero-difunctionalization of 1,3-enynes using electrochemistry. This new method is mild, selective, and general, allowing for the silyl-, germanyl-, and stannyl-alkylation of enynes. Various chlorosilanes as well as chlorogermans, and chlorostannanes can be successfully used in combination with aryl/alkyl-substituted 1,3-enynes and primary, secondary, and tertiary alkyl bromides in the electroreductive coupling.

Original languageEnglish (US)
JournalAngewandte Chemie - International Edition
StateAccepted/In press - 2023

Bibliographical note

Funding Information:
This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4405).

Publisher Copyright:
© 2023 Wiley-VCH GmbH.


  • 1,3-Enynes
  • Alkyl Halides
  • Chlorosilanes
  • Electrochemistry
  • Nickel

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)


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