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Nucleophile- or Light-Induced Synthesis of 3-Substituted Phthalides from 2-Formylarylketones
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    Nucleophile- or Light-Induced Synthesis of 3-Substituted Phthalides from 2-Formylarylketones
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    Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany
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    Organic Letters

    Cite this: Org. Lett. 2012, 14, 9, 2338–2341
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    https://doi.org/10.1021/ol300757m
    Published April 22, 2012
    Copyright © 2012 American Chemical Society

    Abstract

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    The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro–Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm).

    Copyright © 2012 American Chemical Society

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    Supporting Information

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    Detailed experimental procedures, characterization data, and copies of 1H and 13C NMR spectra of all phthalides prepared. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cited By

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    35. Dario C. Gerbino, Daniel Augner, Nikolay Slavov, Hans‐Guenther Schmalz. ChemInform Abstract: Nucleophile‐ or Light‐Induced Synthesis of 3‐Substituted Phthalides from 2‐Formylarylketones.. ChemInform 2012, 43 (35) https://doi.org/10.1002/chin.201235100

    Organic Letters

    Cite this: Org. Lett. 2012, 14, 9, 2338–2341
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol300757m
    Published April 22, 2012
    Copyright © 2012 American Chemical Society

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