Effect of oxygen substituents on the regioselectivity of the Pd-assisted biaryl coupling reaction of benzanilides

Takashi Harayama; Yuko Kawata; Chie Nagura; Tomonori Sato; Taeko Miyagoe; Hitoshi Abe; Yasuo Takeuchi

doi:10.1016/j.tetlet.2005.06.167

Effect of oxygen substituents on the regioselectivity of the Pd-assisted biaryl coupling reaction of benzanilides

Takashi Harayama, Yuko Kawata, Chie Nagura, Tomonori Sato, Taeko Miyagoe, Hitoshi Abe, Yasuo Takeuchi

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

Abstract

This study investigated the effect of oxygen substituents in the benzoyl part of N-(2-iodophenyl)benzamide on the coupling position in its Pd-assisted biaryl coupling reaction. Benzamide with methylenedioxy and acyloxy 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)	6091-6094
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2005.06.167
Publication status	Published - Sep 5 2005

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "This study investigated the effect of oxygen substituents in the benzoyl part of N-(2-iodophenyl)benzamide on the coupling position in its Pd-assisted biaryl coupling reaction. Benzamide with methylenedioxy and acyloxy 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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AU - Harayama, Takashi

AU - Kawata, Yuko

AU - Nagura, Chie

AU - Sato, Tomonori

AU - Miyagoe, Taeko

AU - Abe, Hitoshi

AU - Takeuchi, Yasuo

PY - 2005/9/5

Y1 - 2005/9/5

N2 - This study investigated the effect of oxygen substituents in the benzoyl part of N-(2-iodophenyl)benzamide on the coupling position in its Pd-assisted biaryl coupling reaction. Benzamide with methylenedioxy and acyloxy 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 in the benzoyl part of N-(2-iodophenyl)benzamide on the coupling position in its Pd-assisted biaryl coupling reaction. Benzamide with methylenedioxy and acyloxy 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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