Iron catalysed nitrosation of olefins to oximes

“…245 An iron(II) bis tetrafluoroborate hexahydrate/dipicolinic acid combination served as the metal salt/ligand system. The authors found that a 5:1 mixture of MeOH-H 2 O to be best for this transformation.…”

Section: C-n Bondsmentioning

confidence: 99%

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

et al. 2016

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Cofactor-mimetic aerobic oxidation has conceptually merged with catalysis of syngas reactions to form a wide range of Markovnikov-selective olefin radical hydrofunctionalizations. We cover the development of the field and review contributions to reaction invention, mechanism and application to complex molecule synthesis. We also provide a mechanistic framework for understanding this compendium of radical reactions.

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“…Lahiri and Maiti further investigated the reaction, and found that a catalyst combination of iron(II) tetrafluoroborate and dipicolinic acid (119) was also effective for the nitrosation of styrene derivatives (Scheme 26 B). [69] A change in reaction solvent from ethanol to a methanol/water mixture (5:1) also proved effective. Once again a hydrogen atmosphere was found to be beneficial.…”

Section: Iron-catalysed Radical-mediated Hydrofunctionalisationsmentioning

confidence: 96%

Iron‐Catalysed Hydrofunctionalisation of Alkenes and Alkynes

2014

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The metal‐catalysed hydrofunctionalisation of alkenes and alkynes provides a convenient and atom‐economic route to diversely functionalised products with control of regio‐, chemo‐ and stereoselectivity. As one of the most abundant elements on earth, iron offers a level of sustainable and long‐term availability that is uncommon for most transition metals. Although iron is commonly found in the oxidation states of +2 and +3, the use of redox‐active ligands has allowed the synthesis and application of low oxidation state iron complexes in catalysis. A broad range of hydrofunctionalisation reactions have been developed by using iron catalysts in a wide variety of oxidation states. Intense development over the past decade has resulted in the development of iron‐catalysed hydroamination, hydroalkoxylation, hydrocarboxylation, hydrothiolation, hydrovinylation, hydrosilylation, hydroboration, hydrophosphination, hydromagnesiation and carbonylation reactions, amongst others. With the field still in its infancy, there is great potential for further developments in the mechanistic understanding and synthetic and industrial applicability of these processes.

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Iron catalysed nitrosation of olefins to oximes

Abstract: Fe(BF4)2·6H2O/2,6-pyridinedicarboxylic acid catalysed nitrosation of a wide variety of substituted styrenes has been developed in the presence of t-BuONO/NaBH4 under H2 pressure (10 bar) in MeOH-H2O (5 : 1) to afford corresponding oximes in good to excellent yields.

Cited by 18 publications

References 56 publications

Iron Catalysis in Organic Synthesis

Iron Catalysis in Organic Synthesis

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

Iron‐Catalysed Hydrofunctionalisation of Alkenes and Alkynes

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