Site-selective cross-coupling of dichlorinated benzo-fused nitrogen-heterocycles with Grignard reagents.
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.
Konishi
Hideyuki
H
School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
Itoh
Tatsuya
T
Manabe
Kei
K
D001554:Benzene / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D017672:Nitrogen Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry
D006571:Heterocyclic Compounds; D017672:Nitrogen Compounds; D010165:Palladium; D001554:Benzene