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Updated: Feb 18, 2026

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Site-selective cross-coupling of dichlorinated benzo-fused nitrogen-heterocycles with Grignard reagents
Hideyuki Konishi1, Tatsuya Itoh, Kei Manabe
1School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
Abstract:
Site-selective cross-coupling of dihaloarenes constitutes a useful method for synthesis of multi-substituted arenes. In this paper, we report the site-selective cross-coupling of dichlorinated benzo-fused nitrogen-heterocycles having two chloro groups on the benzene ring. These dichlorinated heterocycles reacted with Grignard reagents in the presence of PdCl(2)(PCy(3))(2) at the positions ortho to the nitrogen-based substituents with high selectivities. A mechanism in which interaction between Lewis acidic Mg and Cl of the ortho position facilitates C-Cl bond cleavage is proposed.
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