Transformation of Silyl-Protected Tetrafluorinated Thia[6]helicene S-Oxide into a Difluorinated Coronene via Induced Desilylation.

ABSTRACT: Sulfur oxidation of thiophene rings is an effective strategy for constructing substituted and polycyclic arenes via Diels-Alder reactions, wherein each thiophene ring is converted into a benzene ring. In the context of converting helicenes into planar coronenes, tetrafluorinated thia[6]helicene S,S-dioxide undergoes a smooth intramolecular Diels-Alder reaction to afford the difluorinated coronene. However, the corresponding S-oxide counterpart is affected by competing side reactions that limit its utility. Herein, we demonstrate that introducing a trimethylsilyl (TMS) group onto the thiophene S-oxide ring suppresses self-condensation and enables more efficient coronene conversion than its S,S-dioxide counterpart. Unexpectedly, the TMS group is removed during the transformation, yielding bo

SUBMITTER: Nakao A 

PROVIDER: S-EPMC12520054 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature