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

doi:10.3987/COM-10-11982

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 journal › Article › peer-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 language	English
Pages (from-to)	1881-1889
Number of pages	9
Journal	Heterocycles
Volume	81
Issue number	8
DOIs	https://doi.org/10.3987/COM-10-11982
Publication status	Published - 2010

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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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.",

author = "Takashi Harayama and Mariko Asai and Taeko Miyagoe and Hitoshi Abe and Yasuo Takeuchi and Ayako Yamaguchi and Shinya Fujii",

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AU - Harayama, Takashi

AU - Asai, Mariko

AU - Miyagoe, Taeko

AU - Abe, Hitoshi

AU - Takeuchi, Yasuo

AU - Yamaguchi, Ayako

AU - Fujii, Shinya

PY - 2010

Y1 - 2010

N2 - 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.

AB - 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.

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ER -

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

Abstract

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