Communication
Catalysis Science & Technology
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Scheme 4 Iron-catalyzed deuterium transfer from d5-EtMgBr.
6 B.-J. Li, D.-G. Yu, C.-L. Sun and Z.-J. Shi, Chem.–Eur. J., 2011,
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¨
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Conclusions
We have shown that the simple pre-catalyst FeCl2 effects rapid
and selective deallylation of various ethers and carbonates. The
reaction conditions tolerate the presence of halide, olefin, ester,
methylthio, allylamine, and benzylether groups. Enhanced
conversion was observed in the presence of nucleophilic neigh-
boring groups or upon employment of N-heterocyclic carbene
ligands. The general protocol allows the selective ether cleavage
and generates volatile by-products (propene, pentene, CO2, etc.),
which obviates the need for laborious product separation. The
ease of operation, mild conditions, and exclusive employment of
commercial reagents make this procedure a valuable tool for
organic synthesis.
´
13 D. Bezier, J.-B. Sortais and C. Darcel, Adv. Synth. Catal.,
2013, 355, 19.
14 An isolated iron carbene complex of the composition
Fe(IPr)Cl2Ádme provided by the group of R. Wolf (University
of Regensburg) gave identical selectivities (Æ1%).
15 For a review, see: (a) J. R. Moss, G. S. Smith and C. H. Kaschula,
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16 For mechanistic postulates of Fe(I) intermediates, see:
We thank Saltigo GmbH, Leverkusen, for financial support.
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than in the aforementioned reports. For postulates of Fe(0)
c
Catal. Sci. Technol.
This journal is The Royal Society of Chemistry 2013