Palladium-Catalyzed Benzofulvenation of o-Arylanilines through C−H Bond Activation by Using Two Diarylacetylenes as an Implicit Benzofulvene

Selvam Raju, Huan Chang Hsiao, Selvakumar Thirupathi, Pei Ling Chen, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

We report the first example of Pd(II)-catalyzed highly step- and atom-economical benzofulvenation through free amine-directed ortho C−H bond activation of o-arylanilines. This paper presents a novel, simple, and efficient approach for the synthesis of benzofulvene derivatives from o-arylaniline substrates through C−H bond activation with two diarylacetylenes as an implicit benzofulvene unit. The reactivity of synthesized benzofulvenes toward oxidation was investigated, and they were shown to transform into phenanthridines, oxabenzofulvenes, and fluorescent polycyclics. 

Original languageEnglish
Pages (from-to)683-689
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume361
Issue number4
DOIs
StatePublished - 19 Feb 2019

Keywords

  • benzofulvene
  • C−H bond activation
  • diphenylacetylene
  • o-arylaniline
  • palladium

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