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Radical Germylzincation of Alkynes

Abstract : The development of a general radical approach for the germylzincation of alkynes as a straightforward route for the preparation of polysubstituted vinylgermanes was the central axis of this work. Within this project, we disclosed that the regio- and stereoselective addition of germanium and zinc across the C‒C triple bond of terminal and internal ynamides was achieved by reaction with a combination of a hydrogermane and diethylzinc in a radical chain process. The key feature of this new approach was the possibility of using the C(sp2)‒Zn bond created as linchpin for subsequent in situ Cu(I)- or Pd(0)-mediated electrophilic substitution with retention of the double bond geometry. Notably, functionalization of the C(sp2)‒Ge bond was also achieved, enhancing germylenamides’ synthetic value. The radical germylzincation approach was further extended to other α-heteroatom-substituted alkynes, as well as more challenging conventional alkynes with excellent levels of stereocontrol. This work marked an important advance over prior art by offering modular access to elaborated di-, tri- and tetrasubstituted vinylgermanes that were not accessible by other methods thus far. From a wider perspective, the generality of the radical elementozincation approach was also preliminarily considered.
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Submitted on : Sunday, October 17, 2021 - 1:01:31 AM
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  • HAL Id : tel-03381504, version 1


Karen de La Vega Hernández. Radical Germylzincation of Alkynes. Organic chemistry. Sorbonne Université, 2019. English. ⟨NNT : 2019SORUS072⟩. ⟨tel-03381504⟩



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