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Journal Articles Journal of the American Chemical Society Year : 2018

Radical Germylzincation of α-Heteroatom-Substituted Alkynes

Abstract

The regio- and stereoselective addition of germanium and zinc across the C–C triple bond of nitrogen-, sulfur-, oxygen-, and phosphorus-substituted terminal and internal alkynes is achieved by reaction with a combination of R3GeH and Et2Zn. Diagnostic experiments support a radical-chain mechanism and the β-zincated vinylgermanes that show exceptional stability are characterized by NMR spectroscopy and X-ray crystallography. The unique feature of this new radical germylzincation reaction is that the C(sp2)–Zn bond formed remains available for subsequent in situ Cu(I)- or Pd(0)-mediated C–C or C–heteroatom bond formation with retention of the double bond geometry. These protocols offer modular access to elaborated tri- and tetrasubstituted vinylgermanes decorated with heteroatom substituents β to germanium that are useful for the preparation of stereodefined alkenes.
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Dates and versions

hal-02337581 , version 1 (29-10-2019)

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Karen de La Vega-Hernández, Elise Romain, Anaïs Coffinet, Kajetan Bijouard, Geoffrey Gontard, et al.. Radical Germylzincation of α-Heteroatom-Substituted Alkynes. Journal of the American Chemical Society, 2018, 140 (50), pp.17632-17642. ⟨10.1021/jacs.8b09851⟩. ⟨hal-02337581⟩
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