FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins

Zotto, Christophe Dal; Michaux, Julien; Zarate-Ruiz, Araceli; Gayon, Eric; Virieux, David; Campagne, Jean‐Marc; Terrasson, Vincent; Pieters, Grégory; Gaucher, Anne; Prim, Damien

doi:10.1016/j.jorganchem.2010.09.031

Cited by 34 publications

(16 citation statements)

References 50 publications

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“…In an analogous fashion, the 8‐membered ring 95 was easily assembled from precursor 94 in 75 % yield. The vinyl ethers thus proved to be exceptionally active substrates in the hydroamination reaction 24. The reaction of the alkene derivative obtained from previously described alcohol 75 required somewhat harsher conditions (80 °C) and provided alkylated 1,4‐oxazepine in 40 % overall yield without purification of the intermediate alkene (Scheme ).…”

Section: Resultsmentioning

confidence: 97%

N‐Protected 1,2‐Oxazetidines as a Source of Electrophilic Oxygen: Straightforward Access to Benzomorpholines and Related Heterocycles by Using a Reactive Tether

Javorskis

Sriubaitė

Bagdžiūnas

et al. 2015

Chemistry A European J

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A hitherto unknown reactivity of a strained four-membered heterocycle, 1,2-oxazetidine, is reported. When reacted with organometallic compounds, this reagent provides electrophilic oxygen with a nitrogen-terminated two-carbon-atom tether. The synthetic versatility of the products obtained was demonstrated in various transformations, leading to efficient synthesis of six-, seven-, and eight-membered heterocyclic systems of pharmaceutical importance.

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Section: Resultsmentioning

confidence: 97%

N‐Protected 1,2‐Oxazetidines as a Source of Electrophilic Oxygen: Straightforward Access to Benzomorpholines and Related Heterocycles by Using a Reactive Tether

Javorskis

Sriubaitė

Bagdžiūnas

et al. 2015

Chemistry A European J

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“…Analysis of the side products from the model system and related reactions led to the identification of compounds 14 – 17 ( Figure 2B ). As 16 and 17 presumably arise from pathways where Fe(acac) 3 behaves as a Lewis acid, 21 we hoped to attenuate the Lewis acidity of the catalyst by increasing the amount of steric shielding of the Fe center. Increasing the size of the substitution on the dione ligands ( 5 – 9 ) led to decreased amounts of 16 , with Fe(dibm) 3 ( 5 , dibm = diisobutyrylmethane) 22 providing the best balance between reactivity and steric shielding.…”

Section: Development Of the Olefin Cross-couplingmentioning

confidence: 99%

Functionalized olefin cross-coupling to construct carbon–carbon bonds

Gui

Yabe

et al. 2014

Nature

400

196

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Carbon–carbon (C–C) bonds form the backbone of many important molecules, including polymers, dyes, and pharmaceutical agents. The development of new methods to create these essential connections in a rapid and practical fashion has been the focus of numerous organic chemists. This endeavor heavily relies on the ability to form C–C bonds in the presence of sensitive functional groups and congested structural environments. Here we report a fundamentally new chemical transformation that allows for the facile construction of highly substituted and uniquely functionalized C–C bonds. Using a simple iron catalyst, an inexpensive silane, and a benign solvent under an ambient atmosphere, heteroatom-substituted olefins are easily merged with electron-deficient olefins to create molecular architectures that were previously difficult or impossible to access. More than sixty examples are presented with a wide array of substrates, demonstrating the unique chemoselectivity and mildness of this simple reaction.

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“…Interestingly, the catalytic activity in water compared to in the organic solvent benzene was essentially the same. In another example, Campagne/Prim and co‐workers used iron(III) chloride salts to promote the intermolecular hydroamination of styrene derivatives using p ‐toluenesulfonamide in 1,4‐dioxane at room temperature . This reaction is notable because iron(III) is air stable and a biologically compatible metal ion.…”

Section: The Future Of Intracellular Chemistrymentioning

confidence: 99%

“…In another example, Campagne/Prim and co-workers used iron(III) chlorides alts to promote the intermolecular hydroamination of styrened erivatives using p-toluenesulfonamide in 1,4-dioxane at room temperature. [111] This reaction is notable because iron(III) is air stable and ab iologically compatible metal ion. Althought hese examples present some deficiencies for use in living environments, such as the need for high temperature or organic solvents, we expect that they could be overcome through reaction optimization and/orcatalyst modifications.…”

Section: The Future Of Intracellular Chemistrymentioning

confidence: 99%

Intracellular Chemistry: Integrating Molecular Inorganic Catalysts with Living Systems

Ngo

Bose

2018

Chemistry A European J

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This concept article focuses on the rapid growth of intracellular chemistry dedicated to the integration of small-molecule metal catalysts with living cells and organisms. Although biological systems contain a plethora of biomolecules that can deactivate inorganic species, researchers have shown that small-molecule metal catalysts could be engineered to operate in heterogeneous aqueous environments. Synthetic intracellular reactions have recently been reported for olefin hydrogenation, hydrolysis/oxidative cleavage, azide-alkyne cycloaddition, allylcarbamate cleavage, C-C bond cross coupling, and transfer hydrogenation. Other promising targets for new biocompatible reaction discovery will also be discussed, with a special emphasis on how such innovations could lead to the development of novel technologies and chemical tools.

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FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins

Cited by 34 publications

References 50 publications

N‐Protected 1,2‐Oxazetidines as a Source of Electrophilic Oxygen: Straightforward Access to Benzomorpholines and Related Heterocycles by Using a Reactive Tether

N‐Protected 1,2‐Oxazetidines as a Source of Electrophilic Oxygen: Straightforward Access to Benzomorpholines and Related Heterocycles by Using a Reactive Tether

Functionalized olefin cross-coupling to construct carbon–carbon bonds

Intracellular Chemistry: Integrating Molecular Inorganic Catalysts with Living Systems

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