Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 19, Pages 4930-4934Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402089
Keywords
alkenes; amines; homogeneous catalysis; hydroamination; iron
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Funding
- ANR JCJC DHAMFER
- Univ Paris Sud
- CNRS
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Despite the growing interest in iron catalysis and hydroamination reactions, iron-catalyzed hydroamination of unprotected primary aliphatic amines and unactivated alkenes has not been reported to date. Herein, a novel well-defined four-coordinate -diketiminatoiron(II) alkyl complex is shown to be an excellent precatalyst for the highly selective cyclohydroamination of primary aliphatic alkenylamines at mild temperatures (70-90 degrees C). Both empirical kinetic analyses and the reactivity of an isolated iron(II) amidoalkene dimer, [LFe(NHCH2CPh2CH2CHCH2)](2) favor a stepwise sigma-insertive mechanism that entails migratory insertion of the pendant alkene into an iron-amido bond associated with a rate-determining aminolysis step.
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