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 journalArticle

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

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phosphine
Regioselectivity
Palladium
Carbon
Oxygen
aniline
benzanilide

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Effect of oxygen substituent in the aniline part of benzanilide on the regioselectivity in direct arylation using palladium-phosphine reagents. / Harayama, Takashi; Asai, Mariko; Miyagoe, Taeko; Abe, Hitoshi; Takeuchi, Yasuo; Yamaguchi, Ayako; Fujii, Shinya.

In: Heterocycles, Vol. 81, No. 8, 2010, p. 1881-1889.

Research output: Contribution to journalArticle

Harayama, Takashi ; Asai, Mariko ; Miyagoe, Taeko ; Abe, Hitoshi ; Takeuchi, Yasuo ; Yamaguchi, Ayako ; Fujii, Shinya. / Effect of oxygen substituent in the aniline part of benzanilide on the regioselectivity in direct arylation using palladium-phosphine reagents. In: Heterocycles. 2010 ; Vol. 81, No. 8. pp. 1881-1889.
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