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Updated: Oct 1, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Modular access to substituted germoles by intramolecular germylzincation
Seydou Kassamba1, Alejandro Perez-Luna2, Franck Ferreira2
1Normandie Univ., UNIROUEN, INSA Rouen, CNRS, Laboratoire COBRA (UMR 6014 & FR 3038), 76000 Rouen, France. muriel.durandetti@univ-rouen.fr.
This study introduces intramolecular alkyne germylzincation using triarylhydrogermanes and diethylzinc to synthesize diverse germoles. The reaction forms a key heteroarylzinc intermediate, enabling further functionalization for novel organometallic compounds.
Area of Science:
- Organometallic Chemistry
- Synthetic Organic Chemistry
Background:
- Germoles are important heterocyclic compounds with diverse applications.
- Efficient synthetic routes to functionalized germoles are crucial for exploring their potential.
Purpose of the Study:
- To develop a novel method for synthesizing germoles via intramolecular alkyne germylzincation.
- To investigate the scope and mechanism of this new transformation.
Main Methods:
- Reaction of triarylhydrogermanes with alkynes in the presence of diethylzinc and azobisisobutyronitrile (AIBN).
- Utilizing a radical initiation pathway for Ge-H bond activation and cyclization.
- Characterization of the resulting germole products.
Main Results:
- Successful synthesis of a wide range of germoles through intramolecular alkyne germylzincation.
- Exclusive formation of 5-endo-dig cyclization products, yielding benzogermoles.
- Generation of a heteroarylzinc intermediate amenable to post-functionalization.
Conclusions:
- Intramolecular alkyne germylzincation provides an effective route to substituted germoles.
- The reaction pathway involves radical initiation and a 5-endo-dig cyclization.
- The generated organozinc intermediate offers opportunities for further synthetic diversification.
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