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.
The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of n class="Chemical">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.
Authors: Trevor V Nykaza; Gen Li; Junyu Yang; Michael R Luzung; Alexander T Radosevich Journal: Angew Chem Int Ed Engl Date: 2020-01-29 Impact factor: 15.336
Authors: Gen Li; Trevor V Nykaza; Julian C Cooper; Antonio Ramirez; Michael R Luzung; Alexander T Radosevich Journal: J Am Chem Soc Date: 2020-03-25 Impact factor: 15.419