Zirconium-Catalyzed Synthesis of Alkenylaminoboranes: From a Reliable Preparation of Alkenylboronates to a Direct Stereodivergent Access to Alkenyl Bromides
2020
Birepinte, Mélodie | Liautard, Virginie | Chabaud, Laurent | Pucheault, Mathieu
A simple procedure has been optimized for the preparation of alkenylaminoborane from alkynes using diisopropylaminoborane and HZrCp₂Cl. Coupled with a magnesium-catalyzed dehydrogenation, it allowed for the use of air- and moisture-stable diisopropylamine. This synthesis has been extended to a one-pot sequence leading directly to bromoalkenes with controlled stereochemistry. As such, it provides an easy, scalable, cheap process to access alkenylboronates and both (E)- and (Z)-bromoalkenes from commercially available alkynes.
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