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Recent Advances in Iron Catalysis
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Recent Advances in Iron Catalysis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organometallic Chemistry".

Deadline for manuscript submissions: closed (31 December 2019) | Viewed by 72645

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Prof. Dr. Hans-Joachim Knölker

E-Mail Website
Guest Editor
Fakultät Chemie, Technische Universität Dresden, Bergstr. 66, 01069 Dresden, Germany
Interests: development of novel synthetic methodologies; natural product chemistry; alkaloids; medicinal chemistry; organometallic chemistry; transition metal-catalyzed reactions

Special Issue Information

Dear Colleagues,

Transition metal-catalyzed reactions play a key role in many transformations that are applied in synthetic organic chemistry. In most of these reactions, noble metals have been used as catalysts, with palladium being the main focus (for example, the Heck coupling, a broad range of palladium(0)-catalyzed cross-coupling reactions, the Wacker oxidation, and many others). Over the last two decades, we have witnessed the development of using more and more first-row transition metals as catalysts for organic reactions, with iron taking the center stage. The driving forces behind this development are not only the high costs of the noble metals, but also their toxicity. Iron is the most abundant transition metal in the Earth’s crust, and thus, it is considerably cheaper than the precious noble metals often used in catalysis. Moreover, iron compounds were involved in many biological processes early on during evolution, and as a consequence, iron exhibits a relatively low toxicity. Because of this low toxicity, iron-catalyzed reactions have become an integral part of environmentally benign sustainable chemistry. However, iron catalysts are investigated not only to replace noble metals, they also offer many applications in synthesis beyond those of classical noble metal catalysts. Several articles in the present Special Issue emphasize the complementarity of iron-catalyzed reactions as compared with reactions catalyzed by noble metals.

The present Special Issue includes a selection of articles demonstrating several intriguing recent developments and the current standing of iron-catalyzed reactions, as well as applications to organic synthesis.

Prof. Dr. Hans-Joachim Knölker
Guest Editor

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

Applications of iron in the following:
• addition reactions
• C–H bond activations
• cross-coupling reactions
• cycloadditions
• isomerizations
• oxidations
• reductions
• substitution reactions

Published Papers (15 papers)

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Research

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12 pages, 3156 KiB  
Article
A DFT Study on FeI/FeII/FeIII Mechanism of the Cross-Coupling between Haloalkane and Aryl Grignard Reagent Catalyzed by Iron-SciOPP Complexes
by Akhilesh K. Sharma and Masaharu Nakamura
Molecules 2020, 25(16), 3612; https://doi.org/10.3390/molecules25163612 - 8 Aug 2020
Cited by 8 | Viewed by 3649
Abstract
To explore plausible reaction pathways of the cross-coupling reaction between a haloalkane and an aryl metal reagent catalyzed by an iron–phosphine complex, we examine the reaction of FeBrPh(SciOPP) 1 and bromocycloheptane employing density functional theory (DFT) calculations. Besides the cross-coupling, we also examined [...] Read more.
To explore plausible reaction pathways of the cross-coupling reaction between a haloalkane and an aryl metal reagent catalyzed by an iron–phosphine complex, we examine the reaction of FeBrPh(SciOPP) 1 and bromocycloheptane employing density functional theory (DFT) calculations. Besides the cross-coupling, we also examined the competitive pathways of β-hydrogen elimination to give the corresponding alkene byproduct. The DFT study on the reaction pathways explains the cross-coupling selectivity over the elimination in terms of FeI/FeII/FeIII mechanism which involves the generation of alkyl radical intermediates and their propagation in a chain reaction manner. The present study gives insight into the detailed molecular mechanic of the cross-coupling reaction and revises the FeII/FeII mechanisms previously proposed by us and others. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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9 pages, 3630 KiB  
Article
Computational Prediction of Chiral Iron Complexes for Asymmetric Transfer Hydrogenation of Pyruvic Acid to Lactic Acid
by Wan Wang and Xinzheng Yang
Molecules 2020, 25(8), 1892; https://doi.org/10.3390/molecules25081892 - 20 Apr 2020
Cited by 1 | Viewed by 2545
Abstract
Density functional theory calculations reveal a formic acid-assisted proton transfer mechanism for asymmetric transfer hydrogenation of pyruvic acid catalyzed by a chiral Fe complex, FeH[(R,R)-BESNCH(Ph)CH(Ph)NH2](η6-p-cymene), with formic acid as the hydrogen provider. [...] Read more.
Density functional theory calculations reveal a formic acid-assisted proton transfer mechanism for asymmetric transfer hydrogenation of pyruvic acid catalyzed by a chiral Fe complex, FeH[(R,R)-BESNCH(Ph)CH(Ph)NH2](η6-p-cymene), with formic acid as the hydrogen provider. The rate-determining step is the hydride transfer from formate anion to Fe for the formation and dissociation of CO2 with a total free energy barrier of 28.0 kcal mol−1. A series of new bifunctional iron complexes with η6-p-cymene replaced by different arene and sulfonyl groups were built and computationally screened as potential catalysts. Among the proposed complexes, we found 1g with η6-p-cymene replaced by 4-isopropyl biphenyl had the lowest free energy barrier of 26.2 kcal mol−1 and excellent chiral selectivity of 98.5% ee. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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13 pages, 3020 KiB  
Article
Iron-Catalyzed Synthesis, Structure, and Photophysical Properties of Tetraarylnaphthidines
by Alexander Purtsas, Sergej Stipurin, Olga Kataeva and Hans-Joachim Knölker
Molecules 2020, 25(7), 1608; https://doi.org/10.3390/molecules25071608 - 1 Apr 2020
Cited by 12 | Viewed by 2663
Abstract
We describe the synthesis and photophysical properties of tetraarylnaphthidines. Our synthetic approach is based on an iron-catalyzed oxidative C–C coupling reaction as the key step using a hexadecafluorinated iron–phthalocyanine complex as a catalyst and air as the sole oxidant. The N,N [...] Read more.
We describe the synthesis and photophysical properties of tetraarylnaphthidines. Our synthetic approach is based on an iron-catalyzed oxidative C–C coupling reaction as the key step using a hexadecafluorinated iron–phthalocyanine complex as a catalyst and air as the sole oxidant. The N,N,N’,N’-tetraarylnaphthidines proved to be highly fluorescent with quantum yields of up to 68%. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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14 pages, 1777 KiB  
Article
A Simple Iron-Catalyst for Alkenylation of Ketones Using Primary Alcohols
by Motahar Sk, Ashish Kumar, Jagadish Das and Debasis Banerjee
Molecules 2020, 25(7), 1590; https://doi.org/10.3390/molecules25071590 - 30 Mar 2020
Cited by 11 | Viewed by 4671
Abstract
Herein, we developed a simple iron-catalyzed system for the α-alkenylation of ketones using primary alcohols. Such acceptor-less dehydrogenative coupling (ADC) of alcohols resulted in the synthesis of a series of important α,β-unsaturated functionalized ketones, having aryl, heteroaryl, alkyl, nitro, nitrile and trifluoro-methyl, as [...] Read more.
Herein, we developed a simple iron-catalyzed system for the α-alkenylation of ketones using primary alcohols. Such acceptor-less dehydrogenative coupling (ADC) of alcohols resulted in the synthesis of a series of important α,β-unsaturated functionalized ketones, having aryl, heteroaryl, alkyl, nitro, nitrile and trifluoro-methyl, as well as halogen moieties, with excellent yields and selectivity. Initial mechanistic studies, including deuterium labeling experiments, determination of rate and order of the reaction, and quantitative determination of H2 gas, were performed. The overall transformations produce water and dihydrogen as byproducts. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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13 pages, 1635 KiB  
Article
Revealing the Iron-Catalyzed β-Methyl Scission of tert-Butoxyl Radicals via the Mechanistic Studies of Carboazidation of Alkenes
by Mong-Feng Chiou, Haigen Xiong, Yajun Li, Hongli Bao and Xinhao Zhang
Molecules 2020, 25(5), 1224; https://doi.org/10.3390/molecules25051224 - 9 Mar 2020
Cited by 10 | Viewed by 4736
Abstract
We describe here a mechanistic study of the iron-catalyzed carboazidation of alkenes involving an intriguing metal-assisted β-methyl scission process. Although t-BuO radical has frequently been observed in experiments, the β-methyl scission from a t-BuO radical into a methyl radical and acetone is still [...] Read more.
We describe here a mechanistic study of the iron-catalyzed carboazidation of alkenes involving an intriguing metal-assisted β-methyl scission process. Although t-BuO radical has frequently been observed in experiments, the β-methyl scission from a t-BuO radical into a methyl radical and acetone is still broadly believed to be thermodynamically spontaneous and difficult to control. An iron-catalyzed β-methyl scission of t-BuO is investigated in this work. Compared to a free t-BuO radical, the coordination at the iron atom reduces the activation energy for the scission from 9.3 to 3.9 ~ 5.2 kcal/mol. The low activation energy makes the iron-catalyzed β-methyl scission of t-BuO radicals almost an incomparably facile process and explains the selective formation of methyl radicals at low temperature in the presence of some iron catalysts. In addition, a radical relay process and an outer-sphere radical azidation process in the iron-catalyzed carboazidation of alkenes are suggested by density functional theory (DFT) calculations. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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9 pages, 1770 KiB  
Article
Solvent-Free Iron(III) Chloride-Catalyzed Direct Amidation of Esters
by Blessing D. Mkhonazi, Malibongwe Shandu, Ronewa Tshinavhe, Sandile B. Simelane and Paseka T. Moshapo
Molecules 2020, 25(5), 1040; https://doi.org/10.3390/molecules25051040 - 26 Feb 2020
Cited by 10 | Viewed by 7111
Abstract
Amide functional groups are prominent in a broad range of organic compounds with diverse beneficial applications. In this work, we report the synthesis of these functional groups via an iron(iii) chloride-catalyzed direct amidation of esters. The reactions are conducted under solvent-free conditions and [...] Read more.
Amide functional groups are prominent in a broad range of organic compounds with diverse beneficial applications. In this work, we report the synthesis of these functional groups via an iron(iii) chloride-catalyzed direct amidation of esters. The reactions are conducted under solvent-free conditions and found to be compatible with a range of amine and ester substrates generating the desired amides in short reaction times and good to excellent yields at a catalyst loading of 15 mol%. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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11 pages, 934 KiB  
Article
Iron-Catalysed C(sp2)-H Borylation Enabled by Carboxylate Activation
by Luke Britton, Jamie H. Docherty, Andrew P. Dominey and Stephen P. Thomas
Molecules 2020, 25(4), 905; https://doi.org/10.3390/molecules25040905 - 18 Feb 2020
Cited by 26 | Viewed by 5976
Abstract
Arene C(sp2)-H bond borylation reactions provide rapid and efficient routes to synthetically versatile boronic esters. While iridium catalysts are well established for this reaction, the discovery and development of methods using Earth-abundant alternatives is limited to just a few examples. [...] Read more.
Arene C(sp2)-H bond borylation reactions provide rapid and efficient routes to synthetically versatile boronic esters. While iridium catalysts are well established for this reaction, the discovery and development of methods using Earth-abundant alternatives is limited to just a few examples. Applying an in situ catalyst activation method using air-stable and easily handed reagents, the iron-catalysed C(sp2)-H borylation reactions of furans and thiophenes under blue light irradiation have been developed. Key reaction intermediates have been prepared and characterised, and suggest two mechanistic pathways are in action involving both C-H metallation and the formation of an iron boryl species. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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18 pages, 1932 KiB  
Article
Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols
by Lin-Yang Wu, Muhammad Usman and Wen-Bo Liu
Molecules 2020, 25(4), 852; https://doi.org/10.3390/molecules25040852 - 14 Feb 2020
Cited by 11 | Viewed by 4486
Abstract
An iron-catalyzed asymmetric oxidative homo-coupling of 2-naphthols for the synthesis of 1,1′-Bi-2-naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron-complex generated in situ from Fe(ClO [...] Read more.
An iron-catalyzed asymmetric oxidative homo-coupling of 2-naphthols for the synthesis of 1,1′-Bi-2-naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron-complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)-N1,N2-di(quinolin-8-yl)cyclohexane-1,2-diamine, L1]. A number of ligands (L2–L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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12 pages, 5864 KiB  
Article
Iron-Catalyzed Cross-Coupling of Bis-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic Investigations
by Lidie Rousseau, Alexandre Desaintjean, Paul Knochel and Guillaume Lefèvre
Molecules 2020, 25(3), 723; https://doi.org/10.3390/molecules25030723 - 7 Feb 2020
Cited by 6 | Viewed by 2829
Abstract
Various substituted bis-(aryl)manganese species were prepared from aryl bromides by one-pot insertion of magnesium turnings in the presence of LiCl and in situ trans-metalation with MnCl2 in THF at −5 °C within 2 h. These bis-(aryl)manganese reagents undergo smooth iron-catalyzed [...] Read more.
Various substituted bis-(aryl)manganese species were prepared from aryl bromides by one-pot insertion of magnesium turnings in the presence of LiCl and in situ trans-metalation with MnCl2 in THF at −5 °C within 2 h. These bis-(aryl)manganese reagents undergo smooth iron-catalyzed cross-couplings using 10 mol% Fe(acac)3 with various functionalized alkenyl iodides and bromides in 1 h at 25 °C. The aryl-alkenyl cross-coupling reaction mechanism was thoroughly investigated through paramagnetic 1H-NMR, which identified the key role of tris-coordinated ate-iron(II) species in the catalytic process. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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17 pages, 3262 KiB  
Communication
Fe-catalyzed Decarbonylative Alkylative Spirocyclization of N-Arylcinnamamides: Access to Alkylated 1-Azaspirocyclohexadienones
by Xiang Peng, Ren-Xiang Liu, Xiang-Yan Xiao and Luo Yang
Molecules 2020, 25(3), 432; https://doi.org/10.3390/molecules25030432 - 21 Jan 2020
Cited by 5 | Viewed by 2492
Abstract
For the convenient introduction of simple linear/branched alkyl groups into biologically important azaspirocyclohexadienones, a practical Fe-catalyzed decarbonylative cascade spiro-cyclization of N-aryl cinnamamides with aliphatic aldehydes to provide alkylated 1-azaspiro-cyclohexadienones was developed. Aliphatic aldehydes were oxidative decarbonylated into primary, secondary and tertiary alkyl [...] Read more.
For the convenient introduction of simple linear/branched alkyl groups into biologically important azaspirocyclohexadienones, a practical Fe-catalyzed decarbonylative cascade spiro-cyclization of N-aryl cinnamamides with aliphatic aldehydes to provide alkylated 1-azaspiro-cyclohexadienones was developed. Aliphatic aldehydes were oxidative decarbonylated into primary, secondary and tertiary alkyl radicals conveniently and allows for the subsequent cascade construction of dual C(sp3)-C(sp3) and C=O bonds via radical addition, spirocyclization and oxidation sequence. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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11 pages, 1880 KiB  
Communication
Cyclopentadienone Iron Tricarbonyl Complexes-Catalyzed Hydrogen Transfer in Water
by Daouda Ndiaye, Sébastien Coufourier, Mbaye Diagne Mbaye, Sylvain Gaillard and Jean-Luc Renaud
Molecules 2020, 25(2), 421; https://doi.org/10.3390/molecules25020421 - 20 Jan 2020
Cited by 10 | Viewed by 3445
Abstract
The development of efficient and low-cost catalytic systems is important for the replacement of robust noble metal complexes. The synthesis and application of a stable, phosphine-free, water-soluble cyclopentadienone iron tricarbonyl complex in the reduction of polarized double bonds in pure water is reported. [...] Read more.
The development of efficient and low-cost catalytic systems is important for the replacement of robust noble metal complexes. The synthesis and application of a stable, phosphine-free, water-soluble cyclopentadienone iron tricarbonyl complex in the reduction of polarized double bonds in pure water is reported. In the presence of cationic bifunctional iron complexes, a variety of alcohols and amines were prepared in good yields under mild reaction conditions. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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13 pages, 3680 KiB  
Article
Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents
by Elwira Bisz and Michal Szostak
Molecules 2020, 25(1), 230; https://doi.org/10.3390/molecules25010230 - 6 Jan 2020
Cited by 14 | Viewed by 5657
Abstract
Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts [...] Read more.
Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)–O bonds. The reaction provides access to alkyl-functionalized aryl benzoates. The examination of various O-coordinating ligands demonstrates the high activity of urea ligands in promoting the cross-coupling versus nucleophilic addition to the ester C(acyl)–O bond. The method showcases the functional group tolerance of iron-catalyzed Kumada cross-couplings. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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Review

Jump to: Research

16 pages, 1280 KiB  
Review
Iron Catalysts in Atom Transfer Radical Polymerization
by Sajjad Dadashi-Silab and Krzysztof Matyjaszewski
Molecules 2020, 25(7), 1648; https://doi.org/10.3390/molecules25071648 - 3 Apr 2020
Cited by 34 | Viewed by 5598
Abstract
Catalysts are essential for mediating a controlled polymerization in atom transfer radical polymerization (ATRP). Copper-based catalysts are widely explored in ATRP and are highly efficient, leading to well-controlled polymerization of a variety of functional monomers. In addition to copper, iron-based complexes offer new [...] Read more.
Catalysts are essential for mediating a controlled polymerization in atom transfer radical polymerization (ATRP). Copper-based catalysts are widely explored in ATRP and are highly efficient, leading to well-controlled polymerization of a variety of functional monomers. In addition to copper, iron-based complexes offer new opportunities in ATRP catalysis to develop environmentally friendly, less toxic, inexpensive, and abundant catalytic systems. Despite the high efficiency of iron catalysts in controlling polymerization of various monomers including methacrylates and styrene, ATRP of acrylate-based monomers by iron catalysts still remains a challenge. In this paper, we review the fundamentals and recent advances of iron-catalyzed ATRP focusing on development of ligands, catalyst design, and techniques used for iron catalysis in ATRP. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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20 pages, 6041 KiB  
Review
On the Use of Iron in Organic Chemistry
by Arnar Guðmundsson and Jan-E. Bäckvall
Molecules 2020, 25(6), 1349; https://doi.org/10.3390/molecules25061349 - 16 Mar 2020
Cited by 32 | Viewed by 8808
Abstract
Transition metal catalysis in modern organic synthesis has largely focused on noble transition metals like palladium, platinum and ruthenium. The toxicity and low abundance of these metals, however, has led to a rising focus on the development of the more sustainable base metals [...] Read more.
Transition metal catalysis in modern organic synthesis has largely focused on noble transition metals like palladium, platinum and ruthenium. The toxicity and low abundance of these metals, however, has led to a rising focus on the development of the more sustainable base metals like iron, copper and nickel for use in catalysis. Iron is a particularly good candidate for this purpose due to its abundance, wide redox potential range, and the ease with which its properties can be tuned through the exploitation of its multiple oxidation states, electron spin states and redox potential. This is a fact made clear by all life on Earth, where iron is used as a cornerstone in the chemistry of living processes. In this mini review, we report on the general advancements in the field of iron catalysis in organic chemistry covering addition reactions, C-H activation, cross-coupling reactions, cycloadditions, isomerization and redox reactions. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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16 pages, 11709 KiB  
Review
C-H Functionalization via Iron-Catalyzed Carbene-Transfer Reactions
by Claire Empel, Sripati Jana and Rene M. Koenigs
Molecules 2020, 25(4), 880; https://doi.org/10.3390/molecules25040880 - 17 Feb 2020
Cited by 40 | Viewed by 6153
Abstract
The direct C-H functionalization reaction is one of the most efficient strategies by which to introduce new functional groups into small organic molecules. Over time, iron complexes have emerged as versatile catalysts for carbine-transfer reactions with diazoalkanes under mild and sustainable reaction conditions. [...] Read more.
The direct C-H functionalization reaction is one of the most efficient strategies by which to introduce new functional groups into small organic molecules. Over time, iron complexes have emerged as versatile catalysts for carbine-transfer reactions with diazoalkanes under mild and sustainable reaction conditions. In this review, we discuss the advances that have been made using iron catalysts to perform C-H functionalization reactions with diazoalkanes. We give an overview of early examples employing stoichiometric iron carbene complexes and continue with recent advances in the C-H functionalization of C(sp2)-H and C(sp3)-H bonds, concluding with the latest developments in enzymatic C-H functionalization reactions using iron-heme-containing enzymes. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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