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Desymmetrization of Dicationic Diboranes by Isomerization Catalyzed by a Nucleophile

Florian Schön, Lutz Greb, Elisabeth Kaifer, Hans‐Jörg Himmel

2020Angewandte Chemie International Edition16 citationsDOIOpen Access PDF

Abstract

Abstract Cationic monoboranes exhibit a rich chemistry. By constrast, only a few cationic diboranes are known, that all are symmetrically substituted. In this work, the first unsymmetrically substituted dicationic diboranes, featuring sp 2 –sp 2 ‐hybridized boron atoms, are reported. The compounds are formed by intramolecular rearrangement from preceding isomeric symmetrically substituted dicationic diboranes, a process that is catalyzed by nucleophiles. From the temperature‐dependence of the isomerization rate, activation parameters for this unprecedented rearrangement are derived. The difference in fluoride ion affinity between the two boron atoms and the bonding situation in these unique unsymmetrical dicationic diboranes are evaluated.

Topics & Concepts

DesymmetrizationIsomerizationNucleophileCatalysisChemistryMedicinal chemistryOrganic chemistryEnantioselective synthesisOrganoboron and organosilicon chemistryBoron Compounds in ChemistryChemical Synthesis and Analysis
Desymmetrization of Dicationic Diboranes by Isomerization Catalyzed by a Nucleophile | Litcius