Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 10, Pages 1593-1599Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000062
Keywords
C-C coupling; chromenes; copper; cyclization; dihydrocoumarins
Categories
Funding
- NNSFC [20972029/20872015]
- NENU [STC08007/07007]
- State Key Laboratory of Fine Chemicals [KF0807]
- analysis and testing foundation of Northeast Normal University
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The synthesis of polyfunctionalized 4H-chromenes 3 and dihydrocoumarins 4 has been developed from the same substrates. Catalyzed by copper(II) bromide (0.3 equiv.), the reactions of the easily available ketene dithioacetals 1 with 2-(hydroxymethyl)phenols 2 lead to 4H-chromenes 3 in high to excellent yields in dichloromethane solvent, whereas, 3,4-trans-disubstituted dihydrocoumarins 4 are obtained in high yields with high diastereoselectivities by prolonging the reaction time or changing the solvent from dichloromethane to acetonitrile.
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