Nikel-Catalyzed Enantioselective C(sp 3)-H Arylation of Ketones with Aryl Ethers via Selective C Ar-O Cleavage to Construct All-Carbon Quaternary Stereocenters

Mingliang Li, Jun Joelle Wang*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

4 Citations (Scopus)

Abstract

We designed thenickel-catalyzed enantioselective C(sp3)-H arylation of ketones with phenol-derived aryl pyrimidyl ethers via selective cleavage of the C(aryl)-O bond to construct all-carbon quaternary stereocenters. This method exhibits good functional group compatibility and broad substrate scope. Drug molecule donepezil can directly transform into corresponding highly optically pure derivatives with this developedmethodology. Mechanistic studies reveal that C(aryl)-O cleavage of aryl pyrimidyl ether probably proceeded by means of an anionic organo-Ni(0) intermediate.

Original languageEnglish
Pages (from-to)2921-2929
Number of pages9
JournalCCS Chemistry
Volume4
Issue number9
DOIs
Publication statusPublished - 5 Sept 2022

Scopus Subject Areas

  • General Chemistry

User-Defined Keywords

  • all-carbon quaternary stereocenter
  • aryl pyrimidyl ether
  • asymmetric arylation
  • C-O cleavage
  • Nickel catalysis

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