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Direct Transition-Metal-Free Intramolecular Arylation of Phenols

Direct transition-metal-free, base-mediated intramolecular arylation of phenols with aryl halides has been developed. In the presence of 2.5 equiv of t-BuOK in dioxane at 140 °C, the intramolecular cyclization of 3-(2-halobenzyloxy)phenols affords 6H-benzo[c]chromenes in high yields. This reaction p...

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Bibliographic Details
Published in:Organic letters 2008-10, Vol.10 (20), p.4625-4628
Main Authors: Bajracharya, Gan B, Daugulis, Olafs
Format: Article
Language:English
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Summary:Direct transition-metal-free, base-mediated intramolecular arylation of phenols with aryl halides has been developed. In the presence of 2.5 equiv of t-BuOK in dioxane at 140 °C, the intramolecular cyclization of 3-(2-halobenzyloxy)phenols affords 6H-benzo[c]chromenes in high yields. This reaction proceeds by an initial formation of a benzyne intermediate followed by an aromatic sp2 C−H functionalization (a formal C−H activation) to form the carbon−carbon bond.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801897m