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Functionalized spirolactones by photoinduced dearomatization of biaryl compounds
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Dalian Institute of Chemical Physics (DICP), China .
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Rekke forfattare: 52019 (engelsk)Inngår i: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 10, nr 12, s. 3681-3686Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2019. Vol. 10, nr 12, s. 3681-3686
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Identifikatorer
URN: urn:nbn:se:su:diva-168611DOI: 10.1039/c8sc05476bISI: 000463759100026PubMedID: 30996963OAI: oai:DiVA.org:su-168611DiVA, id: diva2:1315261
Tilgjengelig fra: 2019-05-13 Laget: 2019-05-13 Sist oppdatert: 2019-05-13bibliografisk kontrollert

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