ol0c00908_si_001.pdf (10.08 MB)
Zirconium-Catalyzed Synthesis of Alkenylaminoboranes: From a Reliable Preparation of Alkenylboronates to a Direct Stereodivergent Access to Alkenyl Bromides
journal contribution
posted on 2020-03-23, 21:29 authored by Mélodie Birepinte, Virginie Liautard, Laurent Chabaud, Mathieu PucheaultA 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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access alkenylboronatesmoisture-stable diisopropylamineReliable PreparationAlkenylaminoboraneDirect Stereodivergent AccessalkenylaminoboranescalableZirconium-Catalyzed Synthesisone-pot sequencestereochemistryAlkenyl BromidesoptimizedbromoalkenediisopropylaminoboraneAlkenylboronatealkynepreparationHZrCp 2 Clmagnesium-catalyzed dehydrogenationsynthesisprocedure
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