Scope and Limitations of the Base-Free Copper(I) Oxide Catalyzed N-Heteroarylation of 1H-(Benz)imidazoles with B-Heteroarylboronic Acids or 2-Heteroaryl-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes

The known, very efficient base‐free copper(I) oxide catalyzed N‐arylation reaction performed in MeOH at room temperature for the synthesis of N‐substituted azoles and amines was extended to the heterocyclic series, i.e., we report herein the base‐free copper(I) oxide catalyzed N‐heteroarylation of 1...

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Bibliographic Details
Published in:Helvetica chimica acta 2013-05, Vol.96 (5), p.853-863
Main Authors: Begouin, Agathe, Queiroz, Maria-João R. P.
Format: Article
Language:English
Subjects:
1H-(Benz)imidazoles
Acids
BuchwaldHartwig reaction
Copper
Ullmann coupling
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Summary:The known, very efficient base‐free copper(I) oxide catalyzed N‐arylation reaction performed in MeOH at room temperature for the synthesis of N‐substituted azoles and amines was extended to the heterocyclic series, i.e., we report herein the base‐free copper(I) oxide catalyzed N‐heteroarylation of 1H‐(benz)imidazole, by means of electron‐rich or electron‐deficient B‐heteroarylboronic acids or 2‐heteroaryl‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolanes (Schemes 1 and 2). Under these conditions, N‐heteroarylated 1H‐(benz)imidazoles were obtained in good to excellent yields (Tables 1 and 2). This is the first time that 2‐heteroaryl‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolanes were used in this type of reaction.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201200310