Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Pd-Catalyzed/Iodide-Promoted α-Arylation of Ketones for the Regioselective Synthesis of Isocoumarins

Pd-Catalyzed/Iodide-Promoted α-Arylation of Ketones for the Regioselective Synthesis of Isocoumarins
Giovanni Maestri, Raimondo Maggi, Nicola Della Ca’, Elena Motti, Alessandra Casnati
A variety of isocoumarins have been synthesized directly from 2-halobenzoates and ketones through a palladium-catalyzed α-arylation step followed by an intramolecular cyclization process. The addition of iodide anions to the reaction mixture increased yields and selectivities especially when 2-bromobenzoates were employed. This phosphine-free one-pot synthesis features a high functional group tolerance and gives access to richly decorated isocoumarins. This general methodology was successful in the total synthesis of Xyridin A, an important natural product with antibacterial and antifungal activity.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01355

DOI: 10.1021/acs.joc.7b01355

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