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Pd-Catalyzed/Iodide-Promoted α‑Arylation of Ketones for the Regioselective Synthesis of Isocoumarins
journal contribution
posted on 2017-07-20, 18:11 authored by Alessandra Casnati, Raimondo Maggi, Giovanni Maestri, Nicola Della Ca’, Elena MottiA 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.
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Regioselective Synthesisreaction mixtureiodide anionsintramolecular cyclization processphosphine-free one-pot synthesis featuresaccessArylationvarietypalladium-catalyzed α- arylation step2- halobenzoatesmethodologyPd-Catalyzed2- bromobenzoatesselectivitieIsocoumarinantifungal activitygroup toleranceXyridinKetoneyieldketoneisocoumarin
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