Some problems in chemistry are so old that we stopped challenging them and accepted them as facts of life. A good example is the epimerization of a chiral centre upon formation of a radical. Take a single enantiomer, make a radical at the chiral centre (often a carbon atom), and within picoseconds the optical purity…
The installation of alkyl substituents through C(sp³)-C(sp³) coupling is in high demand in synthetic and medicinal chemistry. While some strategies towards this goal employ Ni-catalysed cross couplings, this transformation remained challenging due to the difficulty of obtaining cross-selectivity between fleeting aliphatic radicals and alkyl electrophiles. Recently published research in JACS followed a two-stage evolution from…
We chemists love building molecular complexity efficiently and in as few steps as possible. This allows us to transform readily accessible compounds into compounds of high value and to explore and access the vast chemical space which is highly relevant to drug discovery, material science and other fields related to synthetic chemistry. One of the…
Although Hetero-Diels-Alder will play a central role, I am not going to speak about gender. Not today. Instead, I would like to highlight another major advancement in organic chemistry that enables synthesis of alkenes from alkynes. Alkynes serve as versatile building blocks in organic synthesis, drug discovery, and materials science. We chemists use them for…
Researchers from The Chinese University of Hong Kong discovered an alternative mechanism in which organo-selenium acts as a C-H hydrogen bond catalyst, enabling (not only) halogenation of arenes. Key highlights✔️ reveals a previously unexplored mechanism✔️ enables efficient electrophilic halogenation with low catalyst loadings✔️ applicable to the late-stage bromination of several drug molecules✔️ organo-catalyst 2c can…
Imagine a scaffold hopping strategy where you don’t have to re-design your synthetic route for each scaffold. You don’t need Jedi tricks nor power of the dark side to achieve that. This has been addressed for 4-arylpyrimidines in a recent publication by Shun Li et al. published in Nature Communications: “Skeletal editing of 4-arylpyrimidines into…
Do you like to Smile? Or perhaps you’re a fan of rearrangement reactions like me? If so, you’ll want to check out this new paper from my former colleague, Srimanta Manna, Ph.D., and his team: “N,N-Disubstituted Anilines Synthesis through Smiles Rearrangement“ 💡 Why it matters:This methodology enables metal-free C–N coupling under mild conditions, and offers…