Strain‐Promoted 1,3‐Dithiolium‐4‐olates/Alkyne Cycloaddition

Ramar Arun Kumar (1) , Manas Pattanayak (1) , Expédite Yen-Pon (1) , Jijy Elyian (1) , Karine Porte (1) , Sabrina Bernard (1) , Margaux Riomet (1) , Pierre Thuéry (2) , Davide Audisio (1) , Frédéric Taran (1)

1 SCBM - Service de Chimie Bio-Organique et de Marquage
2 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)

We report the reactivity of mesoionic 1,3-dithiolium-4-olates towards strained alkynes leading to thiophene cycloaddition products. In the process, we discovered the potential of these dipoles towards orthogonal reaction with azides allowing efficient double ligation reactions. We also developed a versatile process to access benzo[c]thiophenes in an unprecedented divergent fashion, which provides a new entry to unconventional poly-aromatic thiophenes.

Keywords: Click chemistry; Cycloaddition; Screening; Mesoionics; Thiophene

Domains: Chemical Sciences; Material chemistry; Chemical Sciences; Organic chemistry

Ramar Arun Kumar, Manas Pattanayak, Expédite Yen-Pon, Jijy Elyian, Karine Porte, et al.. Strain‐Promoted 1,3‐Dithiolium‐4‐olates/Alkyne Cycloaddition. Angewandte Chemie, 2019, 131, pp.14686-14690. ⟨10.1002/ange.201908052⟩. ⟨cea-02265800⟩