Palladium-Catalyzed Selective Aryl Ring C–H Activation of N-Acyl-2-aminobiaryls: Efficient Access to Multiaryl-Substituted Naphthalenes

Pratheepkumar Annamalai, Wu Yin Chen, Selvam Raju, Kou Chi Hsu, Nitinkumar Satyadev Upadhyay, Chien Hong Cheng*, Shih-Ching Chuang

*Corresponding author for this work

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

Palladium-catalyzed cycloaromatization of N-acyl-2-aminobiaryls, through a sequence of ortho C−H bond activation/alkyne insertion/meta C−H bond activation/alkyne insertion, was developed. An efficient synthesis of multiaryl-substituted naphthalenes, N-[2-(5,6,7,8-tetraarylnaphthalen-1-yl)aryl]acetamides, was demonstrated using molecular oxygen as the sole oxidant. Furthermore, through Buchwald's synthetic protocol, two compounds were converted into corresponding fluorescent carbazoles in 30–40% yield by intramolecular C−N bond formation. (Figure presented.).

Original languageEnglish
Pages (from-to)3642-3648
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number22
DOIs
StatePublished - 1 Jan 2016

Keywords

  • alkynes
  • aromatic homologation
  • C–H activation
  • naphthalenes
  • palladium

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