Catalytic Cascade Access to Biaryl-2-Methyl Acetates from Pyruvate O-Arylmethyl Ketoximes via the Palladium-Catalyzed C(sp2)H Bond Arylation and C−O Bond Solvolysis

Ling Yan Shao, Li Hao Xing, Ying Guo, Kun Kun Yu, Wei Wang, Hong Wei Liu, Dao Hua Liao, Ya Fei Ji

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

A catalytic cascade has been developed for the synthesis of biaryl-2-methyl acetates via a palladium-catalyzed ortho-C(sp2)−H bond arylation of pyruvate O-arylmethyl ketoximes with aryl iodides followed by a solvolysis, in which the pyruvic ketoxime ester as a new auxiliary is employed to direct the C(sp2)−H bond activation. The straightforward treatment of O-arylmethyl hydroxylamines and ethyl pyruvate with aryl iodides also provides the target products in a one-pot fashion. Furthermore, the new palladacycle intermediate is unambiguously confirmed by single-crystal X-ray diffraction analysis. A plausible reaction pathway is proposed for the Pd-catalyzed arylation-acetolysis sequence. (Figure presented.).

Original languageEnglish (US)
Pages (from-to)2925-2937
Number of pages13
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number15
DOIs
StatePublished - Aug 6 2018
Externally publishedYes

Keywords

  • C(sp)−H bond activation
  • arylation
  • biaryl-2-methyl acetates
  • pyruvate ketoximes
  • solvolysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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