Coupling of thiols and aromatic halides promoted by diboron derived super electron donors

We have proven that pyridine-boryl complexes can be used as superelectron donors to promote the coupling of thiols and aromatic halides through a S(RN)1 mechanism. The reaction is efficient for a broad substrate scope, tolerating heterocycles including pyridines, enolizable or reducible functional groups. The method has been applied to intermediates in drug synthesis as well as interesting functionalized polythioethers through a controlled and consecutive intramolecular electron transfer process.

Automated summary

The study demonstrates that pyridine-boryl complexes can be utilized as super-electron donors to facilitate the coupling of thiols and aromatic halides via a S(RN)1 mechanism. The reaction shows high efficiency with a wide substrate scope, tolerating heterocycles and various functional groups, and has potential applications in drug synthesis and functionalized polythioethers.