Article Dans Une Revue Organic Letters Année : 2015

Stereodivergent Hydrogermylations of α-Trifluoromethylated Alkynes and Their Applications in Cross-Coupling Reactions

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 applicable routes to (Z)-and (E)-α-CF 3 -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.

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hal-05017008 , version 1 (02-04-2025)

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Stéphane Schweizer, Cédric Tresse, Philippe Bisseret, Jacques Lalevée, Gwilherm Evano, et al.. Stereodivergent Hydrogermylations of α-Trifluoromethylated Alkynes and Their Applications in Cross-Coupling Reactions. Organic Letters, 2015, 17 (7), pp.1794-1797. ⟨10.1021/acs.orglett.5b00579⟩. ⟨hal-05017008⟩
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