Zirconium-Catalyzed Synthesis of Alkenylaminoboranes: From a Reliable Preparation of Alkenylboronates to a Direct Stereodivergent Access to Alkenyl Bromides
Mélodie Birepinte, Virginie Liautard, Laurent Chabaud, Mathieu Pucheault
Abstract
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.
Topics & Concepts
ChemistryDehydrogenationCatalysisZirconiumMagnesiumCombinatorial chemistrySequence (biology)Organic chemistryBiochemistryOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis