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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 SostenibilitÓ Ambientale (SCVSA), UniversitÓ di Parma, Parco Area delle Scienze, 17/A, 43124 Parma, Italy, Email: nicola.dellacaunipr.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 (free Supporting Information)


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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

isocoumarins


ID: J42-Y2017