Exploiting Aryl Mesylates and Tosylates in Catalytic Mono-α-arylation of Aryl- and Heteroarylketones

Wai Chung Fu, Chau Ming So, On Ying Yuen, Irene Toi Chuk Lee, Fuk Yee Kwong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

26 Citations (Scopus)

Abstract

The first general palladium catalyst for the catalytic mono-α-arylation of aryl- and heteroarylketones with aryl mesylates and tosylates is described. The newly developed indolyl-derived phosphine ligand L7 has been identified to promote this reaction efficiently. The key to success is attributed to the enhanced steric congestion of the catalyst and effective oxidative addition of the C(Ar)-OMs bond. In the presence of Pd(OAc)2(0.25-2.5 mol %) and L7, selective monoarylations are achieved with ample reaction scope and product yields up to 95%. Importantly, we demonstrated the applicability of this protocol with the modification of biological phenolic compounds, rendering it amenable for functionalization of phenolic (pro)drugs.
Original languageEnglish
Pages (from-to)1872-1875
Number of pages4
JournalOrganic Letters
Volume18
Issue number8
DOIs
Publication statusPublished - 15 Apr 2016

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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