Making Fe(BPBP)-catalyzed C-H and C[double bond, length as m-dash]C oxidations more affordable.
Making Fe(BPBP)-catalyzed C-H and C[double bond, length as m-dash]C oxidations more affordable.
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 sp(3) 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.
- Utrecht University Netherlands
- University Museum Utrecht Netherlands
Biological Products, Pyrrolidines, Molecular Structure, Pyridines, Epoxy Compounds, Ferrous Compounds, Hydrogen Peroxide, Oxidation-Reduction, Catalysis, Hydrocarbons
Biological Products, Pyrrolidines, Molecular Structure, Pyridines, Epoxy Compounds, Ferrous Compounds, Hydrogen Peroxide, Oxidation-Reduction, Catalysis, Hydrocarbons
10 Research products, page 1 of 1
- 2021IsAmongTopNSimilarDocuments
- 2013IsAmongTopNSimilarDocuments
- 2012IsAmongTopNSimilarDocuments
- 2021IsAmongTopNSimilarDocuments
- 2014IsAmongTopNSimilarDocuments
- 2012IsAmongTopNSimilarDocuments
citations This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).33 popularity This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.Top 10% influence This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).Top 10% impulse This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.Top 10%
