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Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes
Author(s) -
Gärtner Annalena,
Marek Matthäus,
Arrowsmith Merle,
Auerhammer Dominic,
Radacki Krzysztof,
Prieschl Dominic,
Dewhurst Rian D.,
Braunschweig Holger
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202101025
Subject(s) - reactivity (psychology) , chemistry , nucleophile , deprotonation , carbene , medicinal chemistry , boron , alkyl , nucleophilic addition , nitrogen , organic chemistry , ion , catalysis , medicine , alternative medicine , pathology
Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of (cyano)dihydroborane precursors. While they display boron‐centered nucleophilic reactivity towards organohalides, generating fully unsymmetrically substituted cyano(hydro)organoboranes, they show cyano‐nitrogen‐centered nucleophilic reactivity towards haloboranes, resulting in the formation of hitherto unknown linear 2‐aza‐1,4‐diborabutatrienes.