Now, chemists at Queen\u2019s University in Canada, led by P. Andrew Evans<\/a> and Gregory Jerkiewicz,<\/a> have developed a simple reaction that uses inexpensive nickel foam<\/a> to do these reduction reactions. The transformation takes advantage of a form of nickel that\u2019s cheap and readily available because it\u2019s used in mass-produced batteries. The reaction tolerates air and moisture, and its discerning reducing power leaves a large number of other functional groups, including halogens, untouched (J. Am. Chem. Soc. 2026, DOI: 10.1021\/jacs.5c19584).<\/p>\n Evans tells C&EN that he thinks the reaction will be particularly useful to medicinal chemists who need to incorporate an aromatic amine into a molecule but also want to maintain a halogen handle for a chemical coupling later in their synthesis. \u201cIt\u2019s a genuinely simple, easy, practical method for doing something that\u2019s often quite hard,\u201d he says.<\/p>\n The process hinges on a sequential two-electron reduction. The hydrogen in the reaction comes from hydrogen chloride generated from acetyl chloride. HCl converts nickel(II) on the surface of the nickel foam\u2014which forms naturally in the presence of air\u2014to Ni(0), which does the reduction. Normally, using Ni(0) requires the use of a glove box.<\/p>\n \u201cHere, what we\u2019re doing is an in situ etching without taking any real precautions to get the Ni(0) to do the two-electron chemistry,\u201d Evans says. He adds that any nickel foam that doesn\u2019t get used can be recovered with a magnet.<\/p>\n “It\u2019s a genuinely simple, easy, practical method for doing something that\u2019s often quite hard.”<\/p>\n P. Andrew Evans, chemistry professor, Queen\u2019s University Canada<\/p>\n Share The chemists show that they can make expensive aromatic amines with a multitude of functional groups from inexpensive nitroaromatics on gram scale. They also use the reaction en route to several drugs, including the antibiotic linezolid (Zyvox), the HIV drug rilpivirine (Edurant), and the cancer drugs enzalutamide (Xtandi) and apalutamide (Erleada).<\/p>\n The reaction does have some limitations, Evans says. It doesn\u2019t work well with nitro heteroaromatics and doesn\u2019t reduce alkyl nitro groups.<\/p>\n Angie Angeles, head of process chemistry at Vertex Pharmaceuticals\u2019 San Diego site, points out that aromatic amines are widely used in pharmaceuticals, agrochemicals, polymers, and fine chemicals, so a simple and environmentally responsible route for making them is important. The fact that the nickel foam \u201cis inexpensive, bench-stable, and compatible with many functional groups makes it especially attractive compared to traditional methods that often require harsher reagents and generate more waste,\u201d she says in an email. \u201cOverall, this looks like a scalable and easy-to-implement method with real potential beyond the academic laboratory.\u201d<\/p>\n Next, Evans says he\u2019s looking to scale up the transformation. He adds that metal foams<\/a> have largely been used in the domain of electrochemistry, but he expects that after other chemists see this paper, they will start trying them out in reactions.<\/p>\n
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