5 years ago

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

Efficient and Mild Ullmann-Type N-Arylation of Amides, Carbamates, and Azoles in Water
Martine Schmitt, Frédéric Bihel, João Xavier de Araújo-Júnior, Pedro G. V. Aquino, Jean-Jacques Bourguignon, Patrick Wagner, Christophe Salomé, Maud Bollenbach
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.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201700832

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