Organic molecules containing nitrogen are prevalent in the pharmaceutical, agrochemical, petrochemical and pigment industries. Not surprisingly, chemists spend a considerable amount of time and resources on the synthesis of amines. Because of their widespread importance and broad utility, it is essential to develop efficient, environmentally friendly methods for the incorporation of nitrogen into organic compounds. David’s work is focused on the development of a practical, general Cu-catalyzed process for the synthesis of amines from alkyl halides and arylhydroxylamines that can be conducted at room temperature. This method utilizes the redox chemistry of copper by coupling the Cu(II)-oxidation of the hydroxylamine with a Cu(I)-reduction of the alkyl halide to render the process catalytic. The carbon radical and nitroso compound generated in this redox cycle react to form the C-N bonds found in the amine products. Key to the sustainability of this approach is the use of earth abundant copper salts as the catalyst, as well as the step economy that significantly reduces the number of synthetic operations previously required.
Advisor: Javier Read de Alaniz