Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 40, Pages 13293-13297Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201808216
Keywords
boranes; borylation; Grignard reagents; Lewis acids; 1,2-migration
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Funding
- University of Manchester
- EPSRC [EP/K039547/1]
- Horizon 2020 Research and Innovation Program [769599]
- Marie Curie Fellowship [703227-DIBOR]
- EPSRC [EP/K039547/1] Funding Source: UKRI
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An intramolecular 1,2-boryl-anion migration from boron to carbon has been achieved by selective activation of the system in [(vinyl)B(2)Pin(2))](-) using soft BR3 electrophiles (BR3=BPh3 or 9-aryl-BBN). The soft character is key to ensure 1,2-migration proceeds instead of oxygen coordination/B-O activation. The BR3-induced 1,2-boryl-anion migration represents a triple borylation of a vinyl Grignard reagent using only B(2)Pin(2) and BR3 and forms differentially protected 1,1,2-triborylated alkanes. Notably, by increasing the steric bulk at the position of the vinyl Grignard reagent used to activate B(2)Pin(2), 1,2-boryl-anion migration can be suppressed in favor of intermolecular {BPin}(-) transfer to BPh3, thus enabling simple access to unsymmetrical sp(2)-sp(3) diboranes.
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