AI Article Synopsis
- A new method enables the regio- and stereoselective addition of germanium and zinc to C-C triple bonds of various alkynes, using RGeH and EtZn.
- This reaction operates through a radical-chain mechanism, leading to stable β-zincated vinylgermanes that have been characterized with NMR and X-ray techniques.
- The formed C(sp)-Zn bond can be used for further bond formation while preserving the geometry, allowing for the creation of complex vinylgermanes that help in synthesizing defined alkenes.
Article 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 RGeH and EtZn. 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(sp)-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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| http://dx.doi.org/10.1021/jacs.8b09851 | DOI Listing |
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