Cu(I)-mediated reductive amination of boronic acids with nitroso aromatics.
[reaction: see text] A mild method for the reductive amination of aryl boronic acids with nitroso aromatic compounds is reported. This C-N bond formation is mediated by a stoichiometric amount of CuCl as both a catalyst and a reducing agent. Alternatively, 10% Cu(I)-3-methylsalicylate (CuMeSal) catalyzes the same reaction in the presence of either ascorbic acid or hydroquinone as the terminal reducing agent. Diarylamines bearing a variety of functional groups can be obtained in good yields.
Yu
Ying
Y
Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
Srogl
Jiri
J
Liebeskind
Lanny S
LS
D000586:Amination; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction
D001897:Boronic Acids; D007202:Indicators and Reagents; D009603:Nitroso Compounds; D003300:Copper