Modular Access to Diverse Chemiluminescent Dioxetane-Luminophores through Convergent Synthesis.

Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: MEDLINE

Publication: <2004-> : Weinheim : Wiley-VCH
Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-

Molecular Probes* ; Singlet Oxygen*; Luminescent Measurements

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.
(© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)

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Keywords: Chemiluminescence; Cross-Coupling; Dioxetanes; Palladium; Synthetic Methods

0 (Molecular Probes)
17778-80-2 (Singlet Oxygen)

Date Created: 20220308 Date Completed: 20220517 Latest Revision: 20240901

20250114

PMC9311660

10.1002/anie.202202187

35258138