An efficient and mild protocol for the α-arylation of ketones mediated by an (imidazol-2-ylidene)palladium(acetate) system

Rohit Singh, Steven P. Nolan

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

The activity of well-defined N-heterocyclic carbene (NHC)-palladium acetate complexes has been studied in the α-arylation of ketones. The enolate was generated in situ via use of slight excess of sodium tert-butoxide as base. The results showed a high activity, allowing for the coupling of non-activated chlorides. The use of hindered substrates provided an avenue for convenient synthesis of various ketone derivatives. The first examples of α-arylation of ketones at room temperature mediated by an NHC-ligated catalyst are also presented.

Original languageEnglish (US)
Pages (from-to)5832-5840
Number of pages9
JournalJournal of Organometallic Chemistry
Volume690
Issue number24-25
DOIs
StatePublished - Dec 1 2005
Externally publishedYes

Bibliographical note

Funding Information:
The National Science Foundation is gratefully acknowledged for financial support of this work and Umicore AG is gratefully acknowledged for the generous gift of Pd(OAc) 2 . We are also grateful to Boehringer-Ingelheim Pharmaceuticals Inc. for an unrestricted grant.

Keywords

  • Arylation
  • Arylchlorides
  • Ketones
  • N-heterocyclic carbenes
  • Palladium

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