Palladium-Catalyzed Direct α-Arylation of Arylacetonitriles with Aryl Tosylates and Mesylates

On Ying Yuen, Xiangmeng Chen, Junyu Wu, Chau Ming So

Research output: Journal article publicationJournal articleAcademic researchpeer-review

3 Citations (Scopus)

Abstract

The first general palladium-catalyzed α-arylation of arylacetonitriles with aryl and heteroaryl sulfonates are reported. Pd(OAc)2 associated with XPhos serves as the effective catalyst to facilitate this reaction. A broad range of electron-rich, -neutral, -deficient, and sterically hindered aryl/heteroaryl tosylates and mesylates are coupled with arylacetonitriles bearing different substituents to give the corresponding products in good to excellent yields. Catalyst loading down to 0.1 mol-% Pd was achieved, and 22 unprecedented compounds were synthesized from 43 demonstrated examples using this method. Its applicability with the modification of biological phenolic compounds was successfully demonstrated. The Pd/XPhos system catalyzed the α-arylation and followed by alkylation in one-pot sequential conditions, resulting in the direct synthesis of compounds containing quaternary center- and deuterium-containing compounds in good to excellent yields.

Original languageEnglish
Pages (from-to)1912-1916
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number12
DOIs
Publication statusPublished - 31 Mar 2020

Keywords

  • Aryl sulfonates
  • Nitriles
  • Palladium
  • Phosphine ligands
  • α-Arylation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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