Facile Access to Substituted 1,4‐Diaza‐2,3‐Diborinines
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- Several bis(dimethylamino)‐substituted 1,4‐diaza‐2,3‐diborinines (DADBs) were synthesized with variable substituents at the backbone nitrogen atoms. By reaction with HCl or BX\(_{3}\) (X=Br, I), these species were successfully converted into their synthetically more useful halide congeners. The high versatility of the generated B−X bonds in further functionalization reactions at the boron centers was demonstrated by means of salt elimination (MeLi) and commutation (NMe\(_{2}\) DADBs) reactions, thus making the DADB system a general structuralSeveral bis(dimethylamino)‐substituted 1,4‐diaza‐2,3‐diborinines (DADBs) were synthesized with variable substituents at the backbone nitrogen atoms. By reaction with HCl or BX\(_{3}\) (X=Br, I), these species were successfully converted into their synthetically more useful halide congeners. The high versatility of the generated B−X bonds in further functionalization reactions at the boron centers was demonstrated by means of salt elimination (MeLi) and commutation (NMe\(_{2}\) DADBs) reactions, thus making the DADB system a general structural motif in diborane(4) chemistry. A total of 18 DADB derivatives were characterized in the solid state by X‐ray diffraction, revealing a strong dependence of the heterocyclic bonding parameters from the exocyclic substitution pattern at boron. According to our experiments towards the realization of a Dipp‐substituted, sterically encumbered DADB, the mechanism of DADB formation proceeds via a transient four‐membered azadiboretidine intermediate that subsequently undergoes ring expansion to afford the six‐membered DADB heterocycle.…
Autor(en): | Torsten Thiess, Moritz Ernst, Thomas Kupfer, Holger BraunschweigORCiD |
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URN: | urn:nbn:de:bvb:20-opus-214650 |
Dokumentart: | Artikel / Aufsatz in einer Zeitschrift |
Institute der Universität: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Sprache der Veröffentlichung: | Englisch |
Titel des übergeordneten Werkes / der Zeitschrift (Englisch): | Chemistry – A European Journal |
Erscheinungsjahr: | 2020 |
Band / Jahrgang: | 26 |
Heft / Ausgabe: | 13 |
Erste Seite: | 2967 |
Letzte Seite: | 2972 |
Originalveröffentlichung / Quelle: | Chemistry – A European Journal 2020, 26(13):2967–2972. DOI: 10.1002/chem.201905356 |
DOI: | https://doi.org/10.1002/chem.201905356 |
Allgemeine fachliche Zuordnung (DDC-Klassifikation): | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Freie Schlagwort(e): | B,N-heterocycles; azadiboretidines; diazadiborinines; diboranes; ring expansion |
Datum der Freischaltung: | 20.04.2021 |
Lizenz (Deutsch): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |