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Reductive Molybdenum‐Catalyzed Direct Amination of Boronic Acids with Nitro Compounds
Author(s) -
SuárezPantiga Samuel,
HernándezRuiz Raquel,
Virumbrales Cintia,
Pedrosa María R.,
Sanz Roberto
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812806
Subject(s) - chemistry , amination , aryl , nitro , catalysis , organic chemistry , combinatorial chemistry , reductive amination , amine gas treating , yield (engineering) , boronic acid , metallurgy , alkyl , materials science
The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C−N coupling. Our methodology has proven to be scalable, air and moisture tolerant, highly chemoselective and engages both aliphatic and aromatic nitro compounds. Moreover, this general and step‐economical synthesis of aromatic secondary amines showcases orthogonality to other aromatic amine syntheses as it tolerates aryl halides and carbonyl compounds.