Dual Gold-Catalyzed Three-Component Reaction: Efficient Synthesis of Indene-Fused Esters, Acids, and Lactones through Gold Vinylidene Intermediates

Congjun Yu, Xiaodong Ma, Bin Chen, Bencan Tang, Robert S. Paton, Guozhu Zhang

Research output: Journal PublicationArticlepeer-review

10 Citations (Scopus)

Abstract

A dual gold(I)-catalyzed three-component reaction was developed to prepare indene-fused carboxylic acid derivatives from diynes, alcohols, and pyridine N-oxides in both inter- and intramolecular fashions. The pyridine N-oxides were found to exhibit distinct selectivity unlike the α-oxo gold carbene intermediates in the well-developed gold-catalyzed oxidative functionalization of alkynes. Experimental studies and DFT calculations support double nucleophilic substitution of a gold vinylidene intermediate.

Original languageEnglish
Pages (from-to)1561-1565
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number11
DOIs
Publication statusPublished - 17 Mar 2017

Keywords

  • Esters
  • Gold
  • Lactones
  • Multicomponent reactions
  • Vinylidenes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Dual Gold-Catalyzed Three-Component Reaction: Efficient Synthesis of Indene-Fused Esters, Acids, and Lactones through Gold Vinylidene Intermediates'. Together they form a unique fingerprint.

Cite this