Tritylium assisted iodine catalysis for the synthesis of unsymmetrical triarylmethanes

Thibaut Courant (1) , Marine Lombard (1) , Dina Boyarskaya (1) , Luc Neuville (1) , Geraldine Masson (1)

1 ICSN - Institut de Chimie des Substances Naturelles

The combined Lewis acid catalytic system, generated from molecular iodine and tritylium tetrafluoroborate effectively catalyzed the Friedel−Crafts (FC) arylation of diarylmethyl sulfides providing an efficient access to various unsymmetrical triarylmethanes. The addition of tritylium and iodine created a more active catalytic system to promote the cleavage of sulfidic C-S bonds. Unsymmetrical triarylmethanes 1 represent an important class of organic molecules due to their occurrence in bioactive natural products (such as muchimangin G-J, 1f melanervin 1k) and pharmaceuticals 1g-i (Figure 1).

Domaines: Chimie; Chimie organique

Thibaut Courant, Marine Lombard, Dina Boyarskaya, Luc Neuville, Geraldine Masson. Tritylium assisted iodine catalysis for the synthesis of unsymmetrical triarylmethanes. Organic & Biomolecular Chemistry, 2020, 18 (33), pp.6502-6508. ⟨10.1039/D0OB01502D⟩. ⟨hal-03009611⟩