Regioselective Hydroalkylation of Vinylarenes by Cooperative Cu and Ni Catalysis

Anne K. Ravn, Martin B. Johansen, Troels Skrydstrup*

*Corresponding author for this work

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

Abstract

Disclosed here is a dual copper and nickel catalytic system with a silyl hydride source for promoting the linear selective hydroalkylation of vinylarenes. This carbon–carbon bond-forming protocol is applied to couple a variety of functionalized vinylarenes with alkyl halides applying a nickel(II) NNN pincer complex in the presence of an NHC-ligated copper catalyst. This combination allows for a 1 mol % loading of the nickel catalyst leading to turnover numbers of up to 72. Over 40 examples are presented, including applications for pharmaceutical diversification. Labeling experiments demonstrated the regioselectivity of the reaction and revealed that the copper catalyst plays a crucial role in enhancing the rate for formation of the reactive linear alkyl nickel complex. Overall, the presented work provides a complimentary approach for hydroalkylation reactions, whilst providing a preliminary mechanistic understanding of the cooperativity between the copper and nickel complexes.

Original languageEnglish
Article numbere202112390
JournalAngewandte Chemie - International Edition
Volume61
Issue4
Number of pages9
ISSN1433-7851
DOIs
Publication statusPublished - 21 Jan 2022

Keywords

  • dual catalysis
  • hydroalkylation
  • metal hydrides
  • regioselectivity
  • vinylarenes

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