Enantioselective Synthesis of Axially Chiral Biaryls via Cu-Catalyzed Acyloxylation of Cyclic Diaryliodonium Salts

Kai Zhu, Kai Xu, Qi Fang, Yi Wang, Bencan Tang, Fengzhi Zhang

Research output: Journal PublicationArticlepeer-review

41 Citations (Scopus)

Abstract

We report here a Cu-catalyzed enantioselective acyloxylation of cyclic diaryliodonium salts. With readily available cyclic diaryliodonium salts and ubiquitous aliphatic or (hetero)aromatic carboxylic acids as the starting materials, various axially chiral acyloxylated 2-iodobiaryls were prepared in excellent yield and with excellent enantioselectivity (mostly 99% yield and 99% ee). Density functional theory calculations were conducted to reveal the stereo- and regioselectivities. This simple reaction protocol can be employed for the late-stage modification of some drug molecules. Finally, by diversity-oriented transformations, these acyloxylated 2-iodobiaryl products can be easily transformed into diverse valuable functionalized biaryls that could be used as chiral ligands or functional materials.

Original languageEnglish
Pages (from-to)4951-4957
Number of pages7
JournalACS Catalysis
Volume9
Issue number6
DOIs
Publication statusPublished - 7 Jun 2019

Keywords

  • Diversity oriented synthesis
  • acyloxylation
  • axially chiral biaryl
  • copper catalysis
  • diaryliodonium salts

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)

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