A catalytic reaction involving the cleavage of two carbon–sulfur bonds in 2,2′-bis(methylthio)-1,1′-biaryl
derivatives is reported. This reaction does not require a transition-metal catalyst
and is promoted by a thiolate anion. Notably, based on DFT calculations, the product-forming
cyclization step is shown to proceed through a concerted nucleophilic aromatic substitution
(CSNAr) mechanism.
Key words
C–S cleavage - C–O cleavage - metathesis - thiophene