Efficient Synthesis of (E)‐Vinylgermanes via Stille Cross‐Coupling Reaction from 1‐Tributylstannyl‐2‐trialkyl(triphenyl)germylethylenes.

David-Quillot, Franck; Marsacq, Didier; Balland, Alexia; Thibonnet, J.; Abarbi, Mohamed; Duchêne, Alain

doi:10.1002/chin.200326187

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“…Hence, the preparation of vinylgermanes is a field of intense ongoing research. A number of approaches have proved suitable for the preparation of vinylgermanes, including electrophilic substitution of vinylmetals with halogermanes, , Pd-catalyzed germylation of vinyl halides, hydro- , or carbometalation of alkynylgermanes, radical substitution of vinylsulfides, -stannanes, or -sulfones, alkene germylation through coupling with hydrogermanes or with vinylgermanes, olefination of acylgermanes, or domino arylgermylation of oxanorbornadiene/retro-Diels–Alder . Yet, the direct synthesis of vinylgermanes from alkynes by carbon–germanium bond-forming addition reactions represents the most straightforward approach and has received the greatest attention.…”

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confidence: 99%

Radical Germylzincation of α-Heteroatom-Substituted Alkynes

et al. 2018

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The regio-and stereoselective addition of germanium and zinc across the CC triple bond of nitrogen-, sulfur-, oxygen-, and phosphorous-substituted terminal and internal alkynes is achieved by reaction with a combination of R 3 GeH and Et 2 Zn. Diagnostic experiments support a radical-chain mechanism and the -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(sp 2)-Zn bond formed remains available for subsequent in situ Cu(I)-or Pd(0)-mediated CC or C-heteroatom bond formation with retention of the double bond geometry. These protocols offer a modular access to elaborated tri-and tetrasubstituted vinylgermanes decorated with heteroatom substituents  to germanium that are useful for the preparation of stereodefined alkenes. Additional data and discussion, experimental details, NMR spectra for new compounds, and X-ray crystal structures (PDF) Crystallographic information files (CIF)

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