Pd-Catalyzed/Iodide-Promoted α-Arylation of Ketones for the Regioselective Synthesis of Isocoumarins
Alessandra Casnati, Raimondo Maggi, Giovanni Maestri , Nicola Della Ca'* and Elena Motti*
*Dipartimento di Scienze Chimiche, della Vita e della
Sostenibilità Ambientale (SCVSA), Università di Parma, Parco Area delle Scienze,
17/A, 43124 Parma, Italy, Email: nicola.dellaca
unipr.it,
elena.mottiunipr.it
A. Casnati, R. Maggi, G. Maestri, N. Della Ca', E. Motti, J. Org. Chem., 2017, 82, 8296-8303.
DOI: 10.1021/acs.joc.7b01355
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Abstract
A palladium-catalyzed α-arylation step followed by an intramolecular cyclization process enables the preparation of various isocoumarins directly from 2-halobenzoates and ketones. In case of 2-bromobenzoates, the addition of iodide anions to the reaction mixture increased yields and selectivities. This phosphine-free one-pot synthesis features a high functional group tolerance and gives access to richly decorated isocoumarins.
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Key Words
ID: J42-Y2017
