Ligand-Controlled Direct γ-C−H Arylation of Aldehydes

Bijin Li, Brianna Lawrence, Guigen Li, Haibo Ge

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

The first example of PdII-catalyzed γ-C(sp3)−H functionalization of aliphatic and benzoheteroaryl aldehydes has been developed using a transient ligand and an external ligand, concurrently. A wide array of γ-arylated aldehydes were readily accessed without preinstalling internal directing groups. The catalytic mechanism was studied by performing deuterium-labelling experiments, which indicated that the γ-C(sp3)−H bond cleavage is the rate-limiting step during the reaction process. This reaction could be performed on a gram scale, and also demonstrated its potential application in the synthesis of new mechanofluorochromic materials with blue-shifted mechanochromic properties.

Original languageEnglish
Pages (from-to)3078-3082
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number8
DOIs
StatePublished - Feb 17 2020

Keywords

  • C−H activation
  • aldehydes
  • mechanochromism
  • palladium
  • reaction mechanisms

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