Dual Photoredox/Cu‐Catalysis Enables Diastereoselective Synthesis of 3‐<i>β</i>‐Ethynyltropanes via Decarboxylative Alkynylation
An efficient decarboxylative alkynylation of a tropane redox‐active ester with terminal alkynes is described, yielding ethynyltropanes with exclusive β ‐configuration. This cost‐effective process utilizes mild, nontoxic copper‐catalyzed, photoinduced reaction conditions. Beyond introducing a novel pathway for the catalytic alkynylation of nortropanes, this method offers a versatile and convergent approach for synthesizing complex nortropane derivatives through further functionalization of the triple bond, including reductions, and inverse demand Diels–Alder reactions.
Authors
- Hichem Ben Jannet (ORCID: https://orcid.org/0000-0001-5858-1803)
- Anis Romdhane (ORCID: https://orcid.org/0000-0002-2962-6416)
- Mayssa Zayene (ORCID: https://orcid.org/0009-0003-9943-3198)
- Vincent Gandon (ORCID: https://orcid.org/0000-0003-1108-9410)
- Pascal Retailleau (ORCID: https://orcid.org/0000-0003-3995-519X)
- Franck Le Bideau (ORCID: https://orcid.org/0000-0003-4365-4525)
- Samir Messaoudi (ORCID: https://orcid.org/0000-0002-4994-9001)
Institutions
- Centre National de la Recherche Scientifique (FR)
- École Polytechnique (FR)
- University of Monastir (TN)
- École Nationale Supérieure de Techniques Avancées (FR)
- Université Paris-Saclay (FR)
- Laboratoire de Synthèse Organique (FR)
- Institut de Chimie Moléculaire et des Matériaux d'Orsay (FR)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2025-06-16
- DOI
- https://doi.org/10.1002/adsc.202500241
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Centre National de la Recherche Scientifique
- Grand Équipement National De Calcul Intensif