1245720-35-7Relevant articles and documents
Radical Germylzincation of α-Heteroatom-Substituted Alkynes
De La Vega-Hernández, Karen,Romain, Elise,Coffinet, Anais,Bijouard, Kajetan,Gontard, Geoffrey,Chemla, Fabrice,Ferreira, Franck,Jackowski, Olivier,Perez-Luna, Alejandro
supporting information, p. 17632 - 17642 (2019/01/04)
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.