The strategic introduction of ring strain into high-energy-density materials (HEDMs) presents a powerful yet underutilized pathway to augment detonation performance and stability. However, most resear...

Decarboxylative amination reactions offer the opportunity to access (hetero)aromatic amines from readily available carboxylic acid starting materials. However, the reliance of the Curtius rearrangemen...

2-Iodoxybenzoic acid (IBX) is a versatile oxidant used in chemical synthesis. It has been employed as a reagent in more than 1400 publications since its initial use as an oxidant described in 1994. Wh...

We report the development of a multifunctional reagent for the direct conversion of carboxylic acids to aldehydes under mild conditions and with exquisite chemoselectivity. These reactions proceed in aqueous solvent at room temperature in 20 min, can be done open to air, require no metal catalysts, and employ near-stoichiometric amounts of both reducing agent and a mild base. No over-reduction, epimerization, or reduction of other reducible functional groups is observed. With this reagent, a broad scope of complex, drug-like aryl and alkyl carboxylic acids can be reduced directly to aldehydes.

We report Lewis acid-catalyzed direct conversion of carboxylic acids into primary amides and nitriles using bis(trimethylsilyl)amine as an ammonia surrogate. With 1.1 equiv of bis(trimethylsilyl)amine...

Deuterium labeling is a key tool used in drug development to observe and prevent metabolism. Here, we report a mild and operationally simple protocol for the synthesis of deuterated cyclopropanes with high levels of deuterium incorporation. This Fe-catalyzed strategy uses dichloromethane-d2 for safe, practical, and diazo-free access to carbene reactivity. A sterically and electronically diverse range of alkenes with varying functional groups are tolerated in this deuterated cyclopropanation. This highly air and water tolerant method complements existing strategies and significantly broadens access to valuable deuterated cyclopropanes, including with applications for the late-stage functionalization of pharmaceuticals.

As an alternative to iridium catalysts, a procedure to access and employ a more earth-adundant Mn2(CO)10-derived pincer complex was successfully demonstrated in the synthesis of a complex pharmaceutically relevant ketone from milligram to 500g scales. Mechanistic studies revealed that the dissociation of CO driven by light is a critical step in forming the active catalyst. This robust and mechanistically informed method reliably promotes hydrogen autotransfer of alcohols, catalyzing a diverse array of C–C and C–N bond formations. This emphasizes the importance of precatalyst selection and understanding catalyst activation to enable rapid and successful uptake of novel methods in sustainable catalysis.