(Diazomethyl)dimethylphosphine Oxide - A Diazoalkane Reagent for [3+2] Cycloadditions.
Nitrogen heterocycles
Phosphorus
cycloaddition
diazoalkanes
pyrazoles
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
22 Feb 2024
22 Feb 2024
Historique:
revised:
08
02
2024
received:
29
11
2023
accepted:
22
02
2024
medline:
22
2
2024
pubmed:
22
2
2024
entrez:
22
2
2024
Statut:
aheadofprint
Résumé
A safe and efficient method for the in-situ preparation of (diazomethyl)dimethylphosphine oxide - a hereto unexplored diazoalkane reagent - is developed. The method is based on the diazotization of the corresponding P(O)Me2-substituted amine (readily available in multigram quantities) in non-aqueous media. The protocol provides the target product as ca. 1.5 M CHCl3 solution which is stable at -18 °C. The utility of the synthesized diazoalkane is illustrated by its [3+2] cycloaddition with electron-poor alkynes and alkenes providing the corresponding P(O)Me2-substituted pyrazoles and pyrazolines with moderate to good efficiency. In this view, the title compound represents and an important extension of medicinally relevant phosphine oxide reagents.
Identifiants
pubmed: 38385831
doi: 10.1002/chem.202303972
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202303972Informations de copyright
© 2024 Wiley-VCH GmbH.