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Functionalized spirolactones by photoinduced dearomatization of biaryl compounds
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry. Dalian Institute of Chemical Physics (DICP), China .
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Number of Authors: 52019 (English)In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 10, no 12, p. 3681-3686Article in journal (Refereed) Published
Abstract [en]

The idea of using biaryl structures to generate synthetic building blocks such as spirolactones is attractive because biaryl structures are abundant in biomass waste streams. However, the inertness of aromatic rings of biaryls makes it challenging to transform them into functionalized structures. In this work, we developed photoinduced dearomatization of nonphenolic biaryl compounds to generate spirolactones. We demonstrate that dearomatization can be performed via either aerobic photocatalysis or anaerobic photooxidation to tolerate specific synthetic conditions. In both pathways, dearomatization is induced by electrophilic attack of the carboxyl radical. The resulting spirodiene radical is captured by either oxygen or water in aerobic and anaerobic systems, respectively, to generate the spirodienone. These methods represent novel routes to synthesize spirolactones from the biaryl motif.

Place, publisher, year, edition, pages
2019. Vol. 10, no 12, p. 3681-3686
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-168611DOI: 10.1039/c8sc05476bISI: 000463759100026PubMedID: 30996963OAI: oai:DiVA.org:su-168611DiVA, id: diva2:1315261
Available from: 2019-05-13 Created: 2019-05-13 Last updated: 2019-05-13Bibliographically approved

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