Lithium zincate-enabled divergent one-pot dual C–C bond formation in thiophenes
We present a lithium zincate-enabled, divergent one-pot synthesis for regioselective dual C-C bond formation in thiophenes. By modifying the zinc coordination environment, a single set of reagents (ZnCl<sub>2</sub>, R<sup>1</sup>Li, and diethyl (5-halo)thenylphosphate) was found to generate two distinct products. This approach extends the versatility of lithium organozincates to regioselective C<sub>Ar</sub>(sp<sup>2</sup>)-C<sub>thienyl</sub>(sp<sup>2</sup>) and C<sub>thenyl</sub>(sp<sup>3</sup>)-C<sub>Ar</sub>(sp<sup>2</sup>) couplings without requiring transition metals and/or arenes pre-activated with a boronic acid.
Authors
- Th. Kauffmann
- Christophe Werlé (ORCID: https://orcid.org/0000-0002-2174-2148)
- Ibrahim Abdellah (ORCID: https://orcid.org/0000-0002-0060-7211)
- Clément Denhez (ORCID: https://orcid.org/0000-0002-0386-9479)
- Kévin Magra
- Alexandre Vasseur (ORCID: https://orcid.org/0000-0003-3294-2417)
- Alexandre Pierret (ORCID: https://orcid.org/0000-0002-5042-021X)
- Héctor S López (ORCID: https://orcid.org/0009-0004-4738-4475)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Max Planck Institute for Chemical Energy Conversion (DE)
- Laboratoire Lorrain de Chimie Moléculaire (FR)
- Université de Lorraine (FR)
- Université de Reims Champagne-Ardenne (FR)
Publication Details
- Journal
- Chemical Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5cc01079a
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Agence Nationale de la Recherche
- Max-Planck-Gesellschaft
- Ministère de l'Education Nationale, de l'Enseignement Superieur et de la Recherche
- Ministère de l'Enseignement Supérieur et de la Recherche