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Nucleophile- or Light-Induced Synthesis of 3-Substituted Phthalides from 2-Formylarylketones

Dario C. Gerbino, Daniel Augner, Nikolay Slavov and Hans-Günther Schmalz*

*Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany, Email: schmalzuni-koeln.de

D. C. Gerbino, D. Augner, N. Slavoy, H.-G. Schmalz, Org. Lett., 2012, 14, 2338-2341.

DOI: 10.1021/ol300757m (free Supporting Information)


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Abstract

A surprisingly facile conversion of 2-formyl-arylketones into 3-substituted phthalides generally proceeds smoothly in DMSO, either in a Cannizarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm).

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proposed mechanism



Key Words

Phtalides, Cannizzaro Reaction, Tishchenko Reaction


ID: J54-Y2012-1410