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Issue 13, 2014
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Making Fe(BPBP)-catalyzed C–H and C[double bond, length as m-dash]C oxidations more affordable

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Abstract

The limited availability of catalytic reaction components may represent a major hurdle for the practical application of many catalytic procedures in organic synthesis. In this work, we demonstrate that the mixture of isomeric iron complexes [Fe(OTf)2(mix-BPBP)] (mix-1), composed of Λ-α-[Fe(OTf)2(S,S-BPBP)] (S,S-1), Δ-α-[Fe(OTf)2(R,R-BPBP)] (R,R-1) and Δ/Λ-β-[Fe(OTf)2(R,S-BPBP)] (R,S-1), is a practical catalyst for the preparative oxidation of various aliphatic compounds including model hydrocarbons and optically pure natural products using hydrogen peroxide as an oxidant. Among the species present in mix-1, S,S-1 and R,R-1 are catalytically active, act independently and represent ca. 75% of mix-1. The remaining 25% of mix-1 is represented by mesomeric R,S-1 which nominally plays a spectator role in both C–H and C[double bond, length as m-dash]C bond oxidation reactions. Overall, this mixture of iron complexes displays the same catalytic profile as its enantiopure components that have been previously used separately in sp3 C–H oxidations. In contrast to them, mix-1 is readily available on a multi-gram scale via two high yielding steps from crude DL/meso-2,2′-bipyrrolidine. Next to its use in C–H oxidation, mix-1 is active in chemospecific epoxidation reactions, which has allowed us to develop a practical catalytic protocol for the synthesis of epoxides.

Graphical abstract: Making Fe(BPBP)-catalyzed C–H and C [[double bond, length as m-dash]] C oxidations more affordable

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Publication details

The article was received on 12 Nov 2013, accepted on 09 Jan 2014 and first published on 09 Jan 2014


Article type: Paper
DOI: 10.1039/C3OB42249F
Citation: Org. Biomol. Chem., 2014,12, 2062-2070
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    Making Fe(BPBP)-catalyzed C–H and C[double bond, length as m-dash]C oxidations more affordable

    V. A. Yazerski, P. Spannring, D. Gatineau, C. H. M. Woerde, S. M. Wieclawska, M. Lutz, H. Kleijn and R. J. M. Klein Gebbink, Org. Biomol. Chem., 2014, 12, 2062
    DOI: 10.1039/C3OB42249F

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