Photo-cycloaddition reactions of vinyldiazo compounds.
Journal
Nature communications
ISSN: 2041-1723
Titre abrégé: Nat Commun
Pays: England
ID NLM: 101528555
Informations de publication
Date de publication:
29 May 2024
29 May 2024
Historique:
received:
18
10
2023
accepted:
26
04
2024
medline:
30
5
2024
pubmed:
30
5
2024
entrez:
29
5
2024
Statut:
epublish
Résumé
Heterocyclic rings are important structural scaffolds encountered in both natural and synthetic compounds, and their biological activity often depends on these motifs. They are predominantly accessible via cycloaddition reactions, realized by either thermal, photochemical, or catalytic means. Various starting materials are utilized for this purpose, and, among them, diazo compounds are often encountered, especially vinyldiazo compounds that give access to donor-acceptor cyclopropenes which engage in [2+n] cycloaddition reactions. Herein, we describe the development of photochemical processes that produce diverse heterocyclic scaffolds from multisubstituted oximidovinyldiazo compounds. High chemoselectivity, good functional group tolerance, and excellent scalability characterize this methodology, thus predisposing it for broader applications. Experimental and computational studies reveal that under light irradiation these diazo reagents selectively transform into cyclopropenes which engage in cycloaddition reactions with various dipoles, while under thermal conditions the formation of pyrazole from vinyldiazo compounds is favored.
Identifiants
pubmed: 38811537
doi: 10.1038/s41467-024-48274-5
pii: 10.1038/s41467-024-48274-5
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
4574Subventions
Organisme : Narodowe Centrum Nauki (National Science Centre)
ID : OPUS UMO-2019/35/B/ST4/03435
Organisme : National Science Foundation (NSF)
ID : CHE 2054845
Organisme : National Science Foundation (NSF)
ID : CHE 2054845
Informations de copyright
© 2024. The Author(s).
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