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 heteroc...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 58; no. 9; pp. 1255 - 1258
Main Authors Konishi, Hideyuki, Itoh, Tatsuya, Manabe, Kei
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 01.09.2010
Pharmaceutical Soc Japan
Japan Science and Technology Agency
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Summary: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 PdCl2(PCy3)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.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.58.1255