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Efficient and Mild Ullmann‐Type N‐Arylation of Amides, Carbamates, and Azoles in Water
Author(s) -
Bollenbach Maud,
Aquino Pedro G. V.,
de AraújoJúnior João Xavier,
Bourguig JeanJacques,
Bihel Frédéric,
Salomé Christophe,
Wagner Patrick,
Schmitt Martine
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700832
Subject(s) - chemistry , aryl , aqueous medium , indazole , combinatorial chemistry , ullmann reaction , indole test , pyridine , catalysis , reaction conditions , organic chemistry , broad spectrum , aqueous solution , alkyl
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.