A Facile and Practical Copper Powder-Catalyzed, Organic Solvent- and Ligand-Free Ullmann Amination of Aryl Halides

Abstract

A facile and practical method that the copper powder-catalyzed Ullmann amination of aryl halides with aqueous methylamine under organic solvent- and ligand-free condition at 100 °C and in air gave N-arylamines as sole products in good to excellent yields. The presence of a small amount of air is essential. Other aliphatic primary amines show good to very high reactivity. Secondary amines and aniline are not reactive. Sensitive substituents (i.e., CHO, MeCO, CN and Cl) are tolerable in the reaction.

The kinetics and mechanisms of organic reactions in liquid ammonia

“…310 Some bromopyridine derivatives give excellent yields in liquid ammonia ( At a similar temperature, the yields of the copper (I) catalysed amination of aryl bromides in liquid ammonia are generally higher than those previously reported by using aqueous ammonia solution or ammonia surrogates as nitrogen source. Furthermore, the amination of aryl bromides requires only 1% copper (I) catalyst in liquid ammonia, which is much lower than those demanded in conventionally used solvents.…”

A BODIPY fluorescence probe modulated by selenoxide spirocyclization reaction for peroxynitrite detection and imaging in living cells

“…A mixture of an 4-fluorobenzaldehyde (12.4 g, 0.1 mol), 60% aqueous ethylamine solution (50 mL, 0.67 mol), and a stirring bar was sealed in a 100 mL autoclave and stirred electromagnetically in an oil bath at 130 C for 15 h [23,24]. The mixture was extracted with ethyl acetate for 3 times (50 mL Â 3), combined organic extracts and washed by 10% hydrochloric acid twice (50 mL Â 2).…”

N-Aryl Lactams by Regioselective Ozonation of N-Aryl Cyclic Amines

“…Solvents were solvent grade from Fluka. Compounds 3 , 11 , and 13 were prepared by Ulmann literature method [29]. Compound 16   was purchased from Acros Organic.…”