Modular Access to Diverse Chemiluminescent Dioxetane-Luminophores through Convergent Synthesis.
Chemiluminescence
Cross-Coupling
Dioxetanes
Palladium
Synthetic Methods
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
23 05 2022
23 05 2022
Historique:
received:
10
02
2022
pubmed:
9
3
2022
medline:
18
5
2022
entrez:
8
3
2022
Statut:
ppublish
Résumé
Adamantyl-dioxetane luminophores are an important class of chemiluminescent molecular probes for diagnostics and imaging. We have developed a new efficient synthetic route for preparation of adamantyl-enolether as precursors for dioxetane chemiluminescent luminophores. The synthesis is convergent, using an unusual Stille cross-coupling reaction employing a stannane-enolether, to directly afford adamantyl-enolether. In a following simple step, the dioxetane is obtained by oxidation of the enolether precursor with singlet-oxygen. The scope of this synthetic route is broad since a large number of haloaryl substrates are either commercially available or easily accessible. Such a late-stage derivatization strategy simplifies the rapid exploration of novel luminogenic molecular structures in a library format and simplifies the synthesis of known dioxetane luminophores. We expect that this new synthetic strategy will be particularly useful in the design and synthesis of yet unexplored dioxetane chemiluminescent luminophores.
Identifiants
pubmed: 35258138
doi: 10.1002/anie.202202187
pmc: PMC9311660
doi:
Substances chimiques
Molecular Probes
0
Singlet Oxygen
17778-80-2
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202202187Informations de copyright
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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