Copper-Catalyzed Annulation–Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process

Tian Shu Zhang, Wen Juan Hao, Pei Jun Cai, Guigen Li, Shu Jiang Tu, Bo Jiang

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

A new Cu(II)-catalyzed annulation–cyanotrifluoromethylation of 1,6-enynes with Togni's reagent and trimethylsilyl cyanide (TMSCN) has been established, enabling the direct construction of trifluoromethylated 1-indanones with an all-carbon quaternary center in good yields. This reaction was performed by using low-cost Cu(OTf)2 as the catalyst and Togni's reagent as both the radical initiator and a CF3 source, providing an efficient protocol for building up an 1-indanone framework with wide functional group compatibility. The reaction mechanism was proposed through a radical triggered addition/5-exo-dig cyclization/oxidation/nucleophilic cascade.

Original languageEnglish
Article number234
JournalFrontiers in Chemistry
Volume8
DOIs
StatePublished - Apr 17 2020

Keywords

  • 1
  • 1-indanones
  • 6-enynes
  • Cu(II) catalysis
  • annulation–difunctionalization
  • cyanotrifluoromethylation

Fingerprint

Dive into the research topics of 'Copper-Catalyzed Annulation–Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process'. Together they form a unique fingerprint.

Cite this