4.7 Article

Iron-catalyzed nucleophilic substitution of allylic acetate

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 17-18, Pages 2641-2646

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200700372

Keywords

allylic substitution; pi-allyl-iron complexes; amine-iron carbonyl complexes; diiron nonacarbonyl; homogeneous catalysis

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The combination of diiron nonacarbonyl and dimethylamine gives an active catalyst for displacement of allylic acetate by diethyl methylmalonate. It was found that among a series of amines, only dimethylamine and morpholine were efficient promoters of the reaction. Solvents such as dimethylformamide (DMF) and N-methylformamide were much superior to tetrahydrofuran, dichloromethane, and ethanol.

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