Group News
The reduction of nitroarenes to anilines is achieved using a nickel foam in acidic ethanol at room temperature. A defining feature of this protocol is its exceptional chemoselectivity, enabling the selective reduction of nitro groups in the presence of aryl halides, nitriles, alkenes, alkynes, and carbonyl derivatives. The selectivity of this method makes it especially powerful for preparing highly functionalized aromatic amines, indispensable motifs in the construction of complex targets, as exemplified by the synthesis of several important drugs and natural products. Structural and surface chemical analyses of the Ni foam before and after in situ activation, using scanning electron microscopy (SEM) and X-ray photoelectron spectroscopy (XPS), reveal its gradual dissolution and the formation of square-shaped pits. The metallic nickel surface formed during activation is required for the reduction.
Prashant Kumar, Mai-Jan Tom, Rebecca L. Grange, Derek Esau, Paul Miller, Gregory Jerkiewicz, P. Andrew Evans, "Chemoselective Reduction of Nitroarenes to Anilines Using a Nickel Foam", J. Am. Chem. Soc. 2026, ASAP
Turning nitroarenes into aromatic amines is a bread-and-butter organic chemistry reaction. And although there are many ways to do this transformation—commonly used to make aromatic amine motifs in drug candidates—there are drawbacks to all of them. more
Halford, B., Nickel foam reaction yields valuable aromatic amines. Chem. Eng. News 2026, April 8.
Although π-allyl chemistry is a cornerstone of catalysis, allylic substitution with unstabilized (“hard”) organometallic nucleophiles has not previously been reviewed as a unified field. This review fills that gap. We survey aryl, alkyl, allyl, alkenyl, alkynyl, benzyl, and allenyl reagents across achiral, stereoselective, and stereospecific processes, highlighting mechanistic insight and reaction design that enable control in these challenging transformations.
Debasis Pal, Kirana D. Veeranna, and P. Andrew Evans, "Advances in Transition Metal-Catalyzed Allylic Substitution with Unstabilized Nucleophiles", Sci China Chem, 2026, 69(1), 94-118.
Yu Zhu and P. Andrew Evans, 6.09 Higher Order Cycloadditions, Editor(s): Paul Knochel, Comprehensive Organic Synthesis (Third Edition), Elsevier, 2025, Pages 545–596.
Hot Paper
We’ve developed a practical, transition-metal-free, enantiospecific alkylation that allows unactivated secondary electrophiles to participate cleanly and predictably—an outcome long viewed as challenging. The reaction is operationally straightforward, uses readily available building blocks, and delivers enantioenriched α-tertiary ketones with high stereochemical fidelity and broad functional-group tolerance. By rethinking how cyanohydrins function as nucleophiles, this work invites a reassessment of the scope of SN2 chemistry, while remaining firmly grounded in everyday synthetic practice.
Jinjin Ma, Hui Li, Jadab Majhi, and P. Andrew Evans, "Stereospecific Transition-Metal-Free Alkylation of Chiral Non-Racemic Secondary Tosylates with Cyanohydrins: Convenient Access to Enantiomerically Enriched α-Tertiary Ketones, Angew. Chem. Int. Ed. 2025, e20674
