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Vinylic Trifluoromethylselenolation via Pd-Catalyzed C−H Activation |
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| Authors: | Arnaud de Zordo-Banliat Dr Kevin Grollier Jordan Vigier Dr Erwann Jeanneau Dr Guillaume Dagousset Dr Bruce Pegot Dr Emmanuel Magnier Dr Thierry Billard |
| Institution: | 1. Institut Lavoisier de Versailles (UMR CNRS 8180), Université Paris-Saclay, UVSQ, CNRS, 78035 Versailles, France
These authors contributed equally to this work.;2. Institute of Chemistry and Biochemistry (ICBMS-UMR CNRS 5246), Univ Lyon, CNRS, Université Lyon 1, CPE Lyon, 1 rue Victor Grignard, 69622 Lyon, France;3. Centre de Diffractométrie Henri Longchambon, Univ Lyon, Université Lyon 1, 5 rue de la Doua, 69100 Villeurbanne, France;4. Institut Lavoisier de Versailles (UMR CNRS 8180), Université Paris-Saclay, UVSQ, CNRS, 78035 Versailles, France |
| Abstract: | Trifluorometylselenolation via C−H activation is barely described in literature. In particular, no such vinylic functionalization has been yet described. Herein, a palladium-catalyzed trifluoromethylselenolation of vinylic C−H bonds is described. The 5-methoxy-8-aminoquinoline has been used as auxiliary directing group to perform this reaction. The reaction gives excellent yields with α-substituted compounds whatever the substituents and a microwave activation can be used to accelerate the reaction. With β-substituted substrates lower yields, but still satisfactory, are obtained. This methodology was also successfully extended to other fluoroalkylselenyl groups. |
| Keywords: | C−H functionalization fluorine selenium trifluoromethylselenolation trifluoromethylselenosulfonate |