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

Ramar Arun Kumar; Manas Pattanayak; Expédite Yen-Pon; Jijy Elyian; Karine Porte; Sabrina Bernard; Margaux Riomet; Pierre Thuéry; Davide Audisio; Frédéric Taran

doi:10.1002/ange.201908052

Journal articles

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, *}

* Corresponding author

1 SCBM - Service de Chimie Bio-Organique et de Marquage

2 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)

NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)

Abstract : 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 Mesoionics Screening Cycloaddition Thiophene

Document type :

Journal articles

Domain :

Chemical Sciences / Material chemistry

Chemical Sciences / Organic chemistry

Complete list of metadata

Cited literature [43 references] Display Hide Download

https://hal-cea.archives-ouvertes.fr/cea-02265800
Contributor : Serge Palacin <>
Submitted on : Monday, August 12, 2019 - 2:43:56 PM
Last modification on : Friday, March 5, 2021 - 3:09:26 PM
Long-term archiving on: : Friday, January 10, 2020 - 9:30:31 PM

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

File

Identifiers

Collections

Citation

Export

Metrics

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

File

Identifiers

Collections

Citation

Export

Share

Metrics