Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 8, Pages 2423-2429Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201103009
Keywords
allylation; catalysis; iron; Michael addition; multicomponent reactions
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Funding
- Studienstiftung des Deutschen Volkes
- Deutsche Forschungsgemeinschaft
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We present herein a versatile and broadly applicable Fe-catalyzed regioselective alkoxy allylation of activated double bonds. Substituted allylic carbonates are converted into the corresponding sigma-enyl Fe complexes by reaction with Bu4N[Fe(CO)3(NO)] (TBAFe) at 30 degrees C. The liberated alkoxide adds to an activated double bond with the generation of a C-nucleophile, which is trapped by the sigma-enyl Fe complex in a regioselective manner. Alternatively, the alkoxide acts as a base in deprotonating an external pronucleophile, which undergoes Michael addition. The method is characterized by a broad functional group tolerance, mild reaction conditions, low catalyst loadings, and high regioselectivities in favor of the ipso-substitution product.
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