par Schweizer, Stéphane;Tresse, Cédric;Bisseret, Philippe;Lalevée, Jacques;Evano, Gwilherm ;Blanchard, Nicolas
Référence Organic letters, 17, page (1794-1979)
Publication Publié, 2015
Référence Organic letters, 17, page (1794-1979)
Publication Publié, 2015
Article révisé par les pairs
Résumé : | The hydrometalation of alkynes with group 14 elements such as tin- or silyl hydrides is a classical transformation in organic synthesis. Strangely, among the group 14 elements, the use of germanium hydrides is rarely seen. Two efficient, stereodivergent, and broadly applicableroutes to (Z)- and (E)-α-CF3-vinylgermanes by regio- and stereoselective hydrogermylation of α-trifluoromethylated alkynes under radical or transition-metal-catalyzed conditions are reported. Furthermore, we demonstrate that the resulting stereodefined fluorinated building blocks are remarkable cross-coupling partners, provided that the vinylgermane is appropriately tuned electronically, as demonstrated by the synthesis of trisubstituted (Z)- and (E)-α-trifluoromethylated alkenes. |