A Redox Transmetalation Step in Nickel-Catalyzed C-C Coupling Reactions

Kerry Ann Green, Aaron P. Honeycutt, Sierra R. Ciccone, Kyle A. Grice, Andreas Baur, Jeffrey L. Petersen, Jessica M. Hoover

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Ni-catalyzed C-H functionalization reactions are becoming efficient routes to access a variety of functionalized arenes, yet the mechanisms of these catalytic C-C coupling reactions are not well understood. Here, we report the catalytic and stoichiometric arylation reactions of a nickel(II) metallacycle. Treatment of this species with silver(I)-aryl complexes results in facile arylation, consistent with a redox transmetalation step. Additionally, treatment with electrophilic coupling partners generates C-C and C-S bonds. We anticipate that this redox transmetalation step may be relevant to other coupling reactions that employ silver salts as additives.

Original languageEnglish (US)
Pages (from-to)6375-6381
Number of pages7
JournalACS Catalysis
Volume13
Issue number9
DOIs
StatePublished - May 5 2023
Externally publishedYes

Bibliographical note

Funding Information:
The authors are grateful to the NIH (1R15GM126514-01) and West Virginia University for financial support of this work. NMR spectroscopy (CHE-1228336) and X-ray diffraction (CHE-1336071) facilities were partially supported by the NSF. The authors thank Melanie Sanford for helpful discussions on related nickelacycle systems.

Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society

Keywords

  • cross-coupling
  • metallacycle
  • nickel
  • redox
  • reductive elimination
  • silver
  • transmetalation

PubMed: MeSH publication types

  • Journal Article

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