Direct Phenylation of nido-B10H14.
J Org Chem
; 87(15): 10034-10043, 2022 08 05.
Article
en En
| MEDLINE
| ID: mdl-35839127
ABSTRACT
As a preliminary step toward its condensation into the porous polymer Activated Borane, the thermolysis of nido-B10H14 (1) in benzene at 200 °C results in the generation of a number of phenylated borane molecular species. The principal product is the new monophenylated compound 5-Ph-nido-B10H13 (2), isolated in 48% yield (based on consumption of 1) and structurally characterized by single-crystal X-ray diffraction analysis, NMR, and mass spectrometry along with other minor products, such as 6-Ph-nido-B10H13 (3), for which we observe UV-light-driven conversion into 2 via a "vertex-flip" mechanism, and novel diphenylated 5,8-Ph2-nido-B10H12 (4). Together, the phenylated derivatives provide a valuable insight into the assembly of Activated Borane and ultimately inform on its structure. The new compounds also display strong blue fluorescence in both solid-state and in solution and are the first examples of the direct phenylation of nido-B10H14, thus opening the door to the straight-forward synthesis of highly luminescent organic-borane hybrid systems.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Boranos
Idioma:
En
Revista:
J Org Chem
Año:
2022
Tipo del documento:
Article
País de afiliación:
República Checa