Electric current jump-starts diamine synthesis

Abstract

To make vicinal diamines, in which neighboring carbons each have an attached amine group, chemists generally expose alkenes to harsh chemical oxidants, which can produce environmentally toxic by-products. Now, researchers have replaced those harsh reactants with a metal catalyst and some electric current to create a safer and less wasteful synthetic route to 1,2-diamines, functional groups that crop up in many pharmaceuticals and stereoselective catalysts (Science 2017, DOI: 10.1126/science.aan6206). The reaction combines abundant starting materials—alkenes and sodium azide—with a manganese catalyst inside a simple electrochemical cell that has a carbon anode and platinum cathode. It adds two equivalents of azide to the alkene C=C bond, generating a 1,2-diazide that can then easily be reduced to a 1,2-diamine. Although electrochemical setups are not common in synthesis labs, they are starting to attract more attention from organic chemistry research groups. One advantage of electrosynthesis is that it giv...