• Citer

Stereodivergent Hydrosilylation, Hydrostannylation and Hydrogermylation of alpha-Trifluoromethylated Alkynes and their Synthetic Applications

par Tresse, Cédric;Schweizer, Stéphane;Bisseret, Philippe;Lalevée, Jacques;Evano, Gwilherm ;Blanchard, Nicolas
Référence Synthesis, 48, page (3317-3330)
Publication Publié, 2016

Article révisé par les pairs

• Accès en ligne
• Détails
• Contenu
• Statistiques

Résumé :

Stereoselective hydrometalation reactions of aryl- and alkyl substituted trifluoromethylated alkynes with triethylsilane, tributylstannane and triphenylgermane have been investigated. (E)-α-CF3-vinylsilanes, stannanes and germanes have been obtained under palladium-catalyzed conditions whereas the corresponding (Z)-α-CF3-vinylgermanes were obtained under radical conditions. These reactions proceed in good to excellent yields and possess a broad functional group tolerance. The applications of the (Z)- and (E)-α-CF3-vinylgermanes in palladium-catalyzed cross-coupling reactions with aryl halide having diverse electronic requirements was also investigated. The corresponding (Z)- and (E)-α-CF3- styrenes were obtained as single isomers, thus demonstrating the utility of these versatile synthons for the synthesis of stereodefined trifluoromethylated alkenes.