Multicomponent Condensation Reactions via ortho-Quinone Methides

Iron­(III) salts promote the condensation of aldehydes or acetals with electron-rich phenols to generate ortho-quinone methides that undergo DielsAlder condensations with alkenes. The reaction sequence occurs in a single vessel to afford benzopyrans in up to 95% yield. The reaction was discovered w...

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Bibliographic Details
Published in:Organic letters 2017-04, Vol.19 (7), p.1878-1881
Main Authors: Allen, Emily E, Zhu, Calvin, Panek, James S, Schaus, Scott E
Format: Article
Language:English
Subjects:
aldehydes
alkenes
benzopyrans
chemical structure
condensation reactions
phenols
salts
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Summary:Iron­(III) salts promote the condensation of aldehydes or acetals with electron-rich phenols to generate ortho-quinone methides that undergo DielsAlder condensations with alkenes. The reaction sequence occurs in a single vessel to afford benzopyrans in up to 95% yield. The reaction was discovered while investigating a two-component strategy using 2-(hydroxy­(phenyl)­methyl)­phenols to access the desired ortho-quinone methide in a DielsAlder condensation. The two-component condensation also afforded the corresponding benzopyran products in yields up to 97%. Taken together, the two- and three-component strategies using ortho-quinone methide intermediates provide efficient access to benzopyrans in good yields and selectivities.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.7b00647