This study introduces the first example of a photocatalytic [3 + 2] cycloaddition reaction to efficiently generate novel chiral imidazolidines using a chiral sulfinamide. A broad range of substrates, including different (S)-N-tert-butanesulfinyl imines and dipole precursors, were found to be compatible, delivering chiral imidazolidines in good yields with high diastereoselectivity (up to 93% yield, up to >25:1 dr). The reaction mechanism was investigated through radical trapping experiments. Furthermore, chiral 1,2-diamines were efficiently obtained with excellent enantioselectivities (up to 100:0 er).

Necessity is the mother of invention. Most synthetic chemistry innovations are driven by our desire to make molecules. In the first half of the 20th century, much of this work was inspired by natural ...

The ever-increasing demand for heat-resistant energetic materials in deep mining and space exploration has led to significant interest in developing new materials with exceptional thermal stability and detonation performance. In this work, a novel heat-resistant energetic compound, 2,5-bis(3,5-dinitro-1H-pyrazol-4-yl)-1,3,4-oxadiazole (3), was achieved through a simple and straightforward method where two 3,5-dinitropyrazole moieties are linked through a 1,3,4-oxadiazole ring. Compound 3, a symmetrical conjugated molecule, demonstrates superior thermal stability (Tdec = 325 °C), good energetic performance (Dv = 8464 m s–1), and improved physical stability (IS = 7.5 J) compared to the industrially used heat-resistant explosive, HNS. The properties of 3 were further optimized by forming energetic salts, 4 and 5. An attempted reaction to synthesize zwitterionic compound 7, having 3,5-dinitropyrazole and 3,5-diamino-1,2,4-triazole ring connected via a C–C bond, resulted in another zwitterionic compound 6. Energetic salts 4 (Tdec = 291 °C) and 5 (Tdec = 275 °C), as well as zwitterionic compound 6 (Tdec = 286 °C), demonstrated excellent decomposition temperatures with good physical stability. The dihydroxylammonium salt (5) (Dv = 8507 m s–1, P = 31.25 GPa) exhibited the best energetic properties, approaching the performance of RDX. The remarkable overall performance of compounds 3-5 makes them suitable candidates for high-performance, heat-resistant explosives.