Expeditious Synthesis of Chiral Imidazolidines and 1,2-Diamines via Photocatalytic [3 + 2] Cycloaddition of Chiral Sulfinamides with Azomethine Ylides 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).

Pretty neat reaction here in #JOCasap a photochemical 3+2 with ylide and chiral sulfinimide to deliver chiral diamines after acidic hydrolysis #ChemSky

Reductive animation without hydrides - this is a very interesting reaction from Hazra (IIT-Delhi) out in #JOCasap where iPrOH as solvent is the reductant and catalyzed by acid (L or B). Scope is limited to anilines at the moment. Interestingly pTSA is almost as good as TMSOTf (cheaper too) #ChemSky

Not sure why the pic didn’t post but here’s the TOC graphic for this excellent #JOCasap paper

1,3,4-Oxadiazole-Bridged 3,5-Dinitropyrazoles: Powerful Alliance toward High Performance and High Thermal Stability 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.

Today in #JOCasap is a paper describing compounds I’d rather not make - Just Say NO and you can say NO2
Kind of surprised the thermal onset temps are that high
#ChemSky #ChemPubs

From Cortisone to Enlicitide: A Journey of Synthetic Chemistry Innovations at Merck 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 ...

One thing you can count on from me is to share great synthesis. While we may be competitors, I’ll highlight this review of #MerckChemistry innovations in #JOCasap from my respected industry colleague and friend @drlcsquare.bsky.social The work here is inspiring and drives us to our best #ChemSky