Unexpected Organo-Catalysis

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 also catalyse other synthetic transformations ❗

Since bromination is one of the most common functionalizations, this catalyst could find broad practical use. Espetially if it becomes commercially avaiable. If you get a chance to use it for your chemistry, let me know how it worked!

I’d also be curious to see how (and if) the reaction would work with alternative imidazolium catalysts. In the paper they tried only one alternative, which didn’t perform well.

🧐 Do you envision this organo-catalyst being useful for other reactions as well ❓
Question for the authors (or anyone): Does it ssmell like rotten eggs ❓

If time permits, the full paper is well worth a read.

#Organocatalysis #Catalysis #MedicinalChemistry #Drugdiscovery #LateStageModification #SyntheticChemistry