Copper-Catalyzed Coupling between ortho-Haloanilines and Lactams/Amides: Synthesis of Benzimidazoles and Telmisartan

An efficient copper-catalyzed synthesis of (annelated) benzimidazoles is reported. This transformation is based on a simple and straightforward one-pot sequence involving a copper-catalyzed cross coupling between o-haloanilines and lactams/amides followed by a subsequent cyclization under acidic con...

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Published inJournal of organic chemistry Vol. 89; no. 8; pp. 5469 - 5479
Main Authors Boquet, Vincent, Sauber, Chris, Beltran, Raphaël, Ferey, Vincent, Rodier, Fabien, Hansjacob, Pierre, Theunissen, Cédric, Evano, Gwilherm
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.04.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CASCADE REACTIONS
AMINES
ONE-POT
N BOND FORMATION
LIGAND
1,2-DISUBSTITUTED BENZIMIDAZOLES
EFFICIENT
DERIVATIVES
CYCLIZATION
O-HALOANILINES
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Summary:An efficient copper-catalyzed synthesis of (annelated) benzimidazoles is reported. This transformation is based on a simple and straightforward one-pot sequence involving a copper-catalyzed cross coupling between o-haloanilines and lactams/amides followed by a subsequent cyclization under acidic conditions. A variety of (annelated) benzimidazoles could be easily obtained in high yields from readily available starting materials, and this procedure could be further applied to the synthesis of the antihypertensive blockbuster drug telmisartan.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02905