Stereodivergent Hydrohalogenation of SCF<sub>3</sub> Alkynes and Cross- Coupling Reactions
SCF<sub>3</sub>-substituted internal alkynes undergo regio- and stereoselective hydrohalogenation to provide the corresponding β-halo-α-SCF<sub>3</sub>-alkenes. The regioselectivity is ensured by the strong polarization of the C≡C triple bond in SCF<sub>3</sub>-alkynes, while the stereoselectivity is governed by the strength of the proton donor and/or by the solvent polarity. The potential of β-iodo-α-SCF<sub>3</sub>-alkenes was illustrated in several cross-coupling, protodeiodination, and cyanation reactions.
Authors
- Dominique Cahard (ORCID: https://orcid.org/0000-0002-8510-1315)
- Vincent Bizet (ORCID: https://orcid.org/0000-0002-0870-1747)
- Norio Shibata (ORCID: https://orcid.org/0000-0002-3742-4064)
- Nicolas Marie (ORCID: https://orcid.org/0000-0002-3217-262X)
- Kim Uyen Ly
Institutions
- Centre National de la Recherche Scientifique (FR)
- Nagoya Institute of Technology (JP)
- Université de Haute-Alsace (FR)
- Normandie Université (FR)
- Laboratoire COBRA (FR)
- Université de Rouen Normandie (FR)
- Université de Strasbourg (FR)
- Institut National des Sciences Appliquées Rouen Normandie (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-16
- DOI
- https://doi.org/10.1021/acs.orglett.4c03760
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.21
Funders
- Indian National Science Academy
- Agence Nationale de la Recherche
- Centre National de la Recherche Scientifique
- Université de Rouen
- Institut National des Sciences Appliquées Rouen
- Institut Carnot Santé Animale
- European Regional Development Fund