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■ 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, and Shinya Fujii

*Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki City, Kagawa 769-2193, Japan

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.