Fe or Fe-NO catalysis? A quantum chemical investigation of the [Fe(CO) 3(NO)]--catalyzed cloke-wilson rearrangement

Johannes E.M.N. Klein; Gerald Knizia; Burkhard Miehlich; Johannes Kästner; Bernd Plietker

doi:10.1002/chem.201402716

Fe or Fe-NO catalysis? A quantum chemical investigation of the [Fe(CO) ₃(NO)]^--catalyzed cloke-wilson rearrangement

Johannes E.M.N. Klein, Gerald Knizia, Burkhard Miehlich, Johannes Kästner, Bernd Plietker

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

Abstract

A quantum chemical investigation of the Bu₄N[Fe(CO) ₃(NO)]-catalyzed Cloke-Wilson rearrangement of vinyl cyclopropanes is reported. It was found that allylic C-C bond activation can proceed through a S_N2 or S_N2-type mechanism. The application of the recently reported intrinsic bond orbital (IBO) method for all structures indicated that one Fe-N π bond is directly involved. Further analysis showed that during the reaction oxidation occurs at the NO ligand exclusively.

Original language	English (US)
Pages (from-to)	7254-7257
Number of pages	4
Journal	Chemistry - A European Journal
Volume	20
Issue number	24
DOIs	https://doi.org/10.1002/chem.201402716
State	Published - Jun 10 2014

Keywords

catalysis
cyclopropane
density functional calculations
iron
quantum chemistry

Publisher link

10.1002/chem.201402716

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title = "Fe or Fe-NO catalysis? A quantum chemical investigation of the [Fe(CO) 3(NO)]--catalyzed cloke-wilson rearrangement",

abstract = "A quantum chemical investigation of the Bu4N[Fe(CO) 3(NO)]-catalyzed Cloke-Wilson rearrangement of vinyl cyclopropanes is reported. It was found that allylic C-C bond activation can proceed through a SN2 or SN2-type mechanism. The application of the recently reported intrinsic bond orbital (IBO) method for all structures indicated that one Fe-N π bond is directly involved. Further analysis showed that during the reaction oxidation occurs at the NO ligand exclusively.",

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T1 - Fe or Fe-NO catalysis? A quantum chemical investigation of the [Fe(CO) 3(NO)]--catalyzed cloke-wilson rearrangement

AU - Klein, Johannes E.M.N.

AU - Knizia, Gerald

AU - Miehlich, Burkhard

AU - Kästner, Johannes

AU - Plietker, Bernd

PY - 2014/6/10

Y1 - 2014/6/10

N2 - A quantum chemical investigation of the Bu4N[Fe(CO) 3(NO)]-catalyzed Cloke-Wilson rearrangement of vinyl cyclopropanes is reported. It was found that allylic C-C bond activation can proceed through a SN2 or SN2-type mechanism. The application of the recently reported intrinsic bond orbital (IBO) method for all structures indicated that one Fe-N π bond is directly involved. Further analysis showed that during the reaction oxidation occurs at the NO ligand exclusively.

AB - A quantum chemical investigation of the Bu4N[Fe(CO) 3(NO)]-catalyzed Cloke-Wilson rearrangement of vinyl cyclopropanes is reported. It was found that allylic C-C bond activation can proceed through a SN2 or SN2-type mechanism. The application of the recently reported intrinsic bond orbital (IBO) method for all structures indicated that one Fe-N π bond is directly involved. Further analysis showed that during the reaction oxidation occurs at the NO ligand exclusively.

KW - catalysis

KW - cyclopropane

KW - density functional calculations

KW - iron

KW - quantum chemistry

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