Efficient and Mild Ullmann‐Type N‐Arylation of Amides, Carbamates, and Azoles in Water

A simple, sustainable, efficient, mild, and low‐cost protocol was developed for d‐glucose‐assisted Cu‐catalyzed Ullmann reactions in water for amides, carbamates, and nitrogen‐containing heterocycles. The reaction was compatible with diverse aryl/heteroaryl iodides, giving highly substituted pyridin...

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Veröffentlicht in:Chemistry : a European journal 2017-10, Vol.23 (55), p.13676-13683
Hauptverfasser: Bollenbach, Maud, Aquino, Pedro G. V., de Araújo‐Júnior, João Xavier, Bourguignon, Jean‐Jacques, Bihel, Frédéric, Salomé, Christophe, Wagner, Patrick, Schmitt, Martine
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Sprache:eng
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Zusammenfassung:A simple, sustainable, efficient, mild, and low‐cost protocol was developed for d‐glucose‐assisted Cu‐catalyzed Ullmann reactions in water for amides, carbamates, and nitrogen‐containing heterocycles. The reaction was compatible with diverse aryl/heteroaryl iodides, giving highly substituted pyridine, indole, or indazole rings. This method offers an attractive alternative to existing protocols, because the reaction proceeds in aqueous media, occurs at or near ambient temperature, and provides the N‐arylated products in good to high yields. Naturally efficient! A protocol for the smooth N‐arylation of amides, carbamates, and azoles is described in water at almost room temperature with the help of inexpensive and commercial catalysts (see figure). The method enables the selective conversion of polyhalogenated aromatics and provides access to pharmacology relevant motifs.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201700832