Palladium-Catalyzed Synthesis of Esters from Arenes through C–H Thianthrenation

The efficient palladium-catalyzed synthesis of esters from readily available arenes has been developed. These C–H bond esterifications were achieved relying on the regioselective thianthrenation to generate the aryl-TT salts, which were treated as reactive electrophilic substrates to couple with phe...

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Veröffentlicht in:Organic letters 2022-08, Vol.24 (32), p.6031-6036
Hauptverfasser: Wang, Mengning, Zhang, Xiaomei, Ma, Mengtao, Zhao, Binlin
Format: Artikel
Sprache:eng
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Zusammenfassung:The efficient palladium-catalyzed synthesis of esters from readily available arenes has been developed. These C–H bond esterifications were achieved relying on the regioselective thianthrenation to generate the aryl-TT salts, which were treated as reactive electrophilic substrates to couple with phenol formate and N-hydroxysuccinimide (NHS) formate giving access to phenol esters and NHS esters, respectively, in the absence of carbon monoxide. A wide range of functional esters could be prepared with high efficiency under this redox-neutral palladium-catalytic condition. Late-stage functionalization and investigations of synthetic applications demonstrated the potential application of the established platform and these products.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02330