Construction of a Diverse Range of Boron Heterocycles via Ring Expansion of a Carboranyl-Substituted 9-Borafluorene.
boroles
carboranes
insertion
medium-ring compounds
ring expansion
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
11 May 2023
11 May 2023
Historique:
received:
20
01
2023
medline:
17
2
2023
pubmed:
17
2
2023
entrez:
16
2
2023
Statut:
ppublish
Résumé
Direct insertion of unsaturated substrates into a five-membered borole ring is a useful method to obtain valuable heterocycles containing one or more three-coordinate boron atoms. A highly Lewis acidic 9-o-carboranyl-9-borafluorene, in which the o-carboranyl substituent is connected via one of the cluster carbon atoms to the boron atom of the 9-borafluorene unit, was found to react with a vast array of unsaturated molecules, such as alkynes, aldehydes and various organic azides, to form larger boraheterocyclic products. The ring expansion reactions of the central borole ring proceed rapidly at room temperature, cementing the role of the o-carboranyl substituent in enhancing the insertion reactivity of 9-borafluorenes.
Identifiants
pubmed: 36794763
doi: 10.1002/chem.202300210
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300210Subventions
Organisme : Julius-Maximilians-Universität Würzburg
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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We thank a reviewer for these insights.
A closely related acetone adduct of 1 displays an 11B NMR signal at 8.8 ppm (see Ref. [9]).