Effect of oxygen substituent in the aniline part of benzanilide on the regioselectivity in direct arylation using palladium-phosphine reagents

Takashi Harayama, Mariko Asai, Taeko Miyagoe, Hitoshi Abe, Yasuo Takeuchi, Ayako Yamaguchi, Shinya Fujii

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

This study investigated the effect of oxygen substituents at the 3'-position in the aniline part of 2-iodobenzanilides on the coupling position in its Pd-assisted direct arylation. Benzanilide with methylenedioxy and acetoxy groups yielded the ortho-product formed predominantly by connection to a more hindered carbon. The mechanism is discussed from the perspectives of both steric and coordinated effects.

Original languageEnglish
Pages (from-to)1881-1889
Number of pages9
JournalHeterocycles
Volume81
Issue number8
DOIs
Publication statusPublished - 2010

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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