scholarly journals On the Use of Iron in Organic Chemistry

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1349 ◽  
Author(s):  
Arnar Guðmundsson ◽  
Jan-E. Bäckvall
Keyword(s):  
Organic Chemistry ◽  
Redox Potential ◽  
Potential Range ◽  
Coupling Reactions ◽  
Base Metals ◽  
Metal Catalysis ◽  
Iron Catalysis ◽  
Cross Coupling Reactions ◽  
Life On Earth ◽  
Palladium Platinum

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.

Withdrawal Notice: Recent Advances in Sonogashira Cross-Coupling Reactions Under Solvent-Free Conditions

2020 ◽  
Vol 24 ◽  
Author(s):  
Teng Wang ◽  
Zongrui Liu ◽  
Songlin Wang ◽  
Esmail Vessally
Keyword(s):  
Organic Chemistry ◽  
Editorial Policy ◽  
Cross Coupling ◽  
Solvent Free ◽  
Coupling Reactions ◽  
Editorial Policies ◽  
Cross Coupling Reactions ◽  
Recent Advances ◽  
Solvent Free Conditions ◽  
Copyright Permission

The article has been withdrawn at the request of editor of the journal Current Organic Chemistry: Bentham Science apologizes to the readers of the journal for any inconvenience this may have caused. The Bentham Editorial Policy on Article Withdrawal can be found at https://benthamscience.com/editorial-policies-main.php BENTHAM SCIENCE DISCLAIMER: It is a condition of publication that manuscripts submitted to this journal have not been published and will not be simultaneously submitted or published elsewhere. Furthermore, any data, illustration, structure or table that has been published elsewhere must be reported, and copyright permission for reproduction must be obtained. Plagiarism is strictly forbidden, and by submitting the article for publication the authors agree that the publishers have the legal right to take appropriate action against the authors, if plagiarism or fabricated information is discovered. By submitting a manuscript, the authors agree that the copyright of their article is transferred to the publishers if and when the article is accepted for publication.

Heterogeneous Metal Catalysis for the Environmentally Benign Synthesis of Medicinally Important Scaffolds, Intermediates, and Building Blocks

2021 ◽  
Vol 25 ◽  
Author(s):  
Maysa Ilamanova ◽  
Maxim Mastyugin ◽  
Christian Schäfer ◽  
Anne Kokel ◽  
Béla Török
Keyword(s):  
Building Blocks ◽  
Metal Catalysts ◽  
Solid Metal ◽  
Coupling Reactions ◽  
Hydrogenation Catalysts ◽  
Metal Catalysis ◽  
Solid Catalysts ◽  
Cross Coupling Reactions ◽  
Benign Synthesis ◽  
Two Sides

: This account provides a broad overview of the application of solid metal catalysts in synthetic chemistry with a focus on the synthesis of medicinally important scaffolds or building blocks. Heterogeneous catalysis is a fundamental contributor to green or sustainable synthesis. Despite this, many synthetic chemists overwhelmingly focus on homogeneous methods, and due to their unfamiliarity with solid catalysts, many would not consider using them. The primary purpose of this work is to bring solid catalysts and their application possibilities to the attention of synthetic chemists in a format that focuses on reactions, thus building a bridge between the two sides for the benefit of sustainable applications and, eventually, the whole society. The two major parts of this account describe the common types of solid metal catalysts and the applications of these catalysts in sustainable synthesis. The first part gives an overview of the major types of solid metal catalysts, including common hydrogenation catalysts to metal nanoparticles. The second and more extensive part illustrates the use of these catalysts in a thematic order based on reaction types, including hydrogenation, hydrogenolysis, oxidation, metathesis, cross-coupling reactions, and hydroformylation.

scholarly journals Iron-catalyzed domino coupling reactions of π-systems

2021 ◽  
Vol 17 ◽  
pp. 2848-2893
Author(s):  
Austin Pounder ◽  
William Tam
Keyword(s):  
Noble Metal ◽  
Environmentally Benign ◽  
Coupling Reactions ◽  
Domino Reactions ◽  
Efficient Synthesis ◽  
Metal Catalysis ◽  
Iron Catalysis ◽  
The Past ◽  
Earth Abundant ◽  
Indispensable Tool

The development of environmentally benign, inexpensive, and earth-abundant metal catalysts is desirable from both an ecological and economic standpoint. Certainly, in the past couple decades, iron has become a key player in the development of sustainable coupling chemistry and has become an indispensable tool in organic synthesis. Over the last ten years, organic chemistry has witnessed substantial improvements in efficient synthesis because of domino reactions. These protocols are more atom-economic, produce less waste, and demand less time compared to a classical stepwise reaction. Although iron-catalyzed domino reactions require a mindset that differs from the more routine noble-metal, homogenous iron catalysis they bear the chance to enable coupling reactions that rival that of noble-metal-catalysis. This review provides an overview of iron-catalyzed domino coupling reactions of π-systems. The classifications and reactivity paradigms examined should assist readers and provide guidance for the design of novel domino reactions.

Protocol for Palladium/N-Heterocyclic Carbene-Catalyzed Suzuki–Miyaura Cross-Coupling of Amides by N–C(O) Activation

Synthesis ◽  
2020 ◽  
Author(s):  
Peng Lei ◽  
Guangchen Li ◽  
Michal Szostak ◽  
Yun Ling ◽  
Jie An ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Room Temperature ◽  
Bond Activation ◽  
Process Development ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Amide Bonds ◽  
Cross Coupling Reactions ◽  
Synthetic Procedure ◽  
Operational Simplicity

AbstractAmides are among the most important and ubiquitous functional groups in organic chemistry and process development. In this Practical Synthetic Procedure, a protocol for the Suzuki–Miyaura cross-coupling of amides by selective N–C(O) bond activation catalyzed by commercially available, air- and moisture-stable palladium/N-heterocyclic carbene (NHC) complexes is described. The procedure described involves [Pd(IPr)(cin)Cl] [IPr = 2,6-(diisopropylphenyl)imidazol-2-ylidene, cin = cinnamyl] at 0.10 mol% at room temperature and is performed on decagram scale. Furthermore, a procedure for the synthesis of amide starting materials is accomplished via selective N-tert-butoxycarbonylation, which is the preferred method over N-acylation. The present protocol carries advantages of operational simplicity, commercial availability of catalysts, and excellent conversions at low catalyst loadings. The method is generally useful for activation of N–C(O) amide bonds in a broad spectrum of amide precursors. The protocol should facilitate the implementation of amide cross-coupling reactions.

Nickel-Catalyzed Paired Electrochemical Cross-Coupling of Aryl Halides with Nucleophiles

Synthesis ◽  
2021 ◽  
Author(s):  
Yong Zhang ◽  
Wenxuan Sun ◽  
Chao Li
Keyword(s):  
Organic Chemistry ◽  
Energy Efficiency ◽  
Anodic Oxidation ◽  
Counter Electrode ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Electrochemical Reactions ◽  
Coupling Reactions ◽  
Atom Economy ◽  
Cross Coupling Reactions

Electrochemistry has recently gained increased attention as a versatile strategy for achieving challenging transformations at the forefront of synthetic organic chemistry. However, most electrochemical transformations only employ one electrode (anodic oxidation or cathodic reduction) to afford the desired products, while the chemistry that occurs at the counter electrode yields stoichiometric waste. In contrast, paired electrochemical reactions can synchronously utilize the anodic and cathodic reactions to deliver the desired product, thus improving the atom economy and energy efficiency of the electrolytic process. This review gives an overview of recent advances in nickel-catalyzed paired electrochemical cross-coupling reactions of aryl/alkenyl halides with different nucleophiles.

scholarly journals α-Arylation of Amides from α-Halo Amides Using Metal-Catalyzed Cross-Coupling Reactions

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 178-184 ◽  
Author(s):  
E. Barde ◽  
A. Guérinot ◽  
J. Cossy
Keyword(s):  
Palladium Catalysis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Nickel Catalysis ◽  
Organometallic Reagents ◽  
Iron Catalysis ◽  
Cross Coupling Reactions ◽  
Metal Catalyzed

Metal-catalyzed α-arylation of amides from α-halo amides with organometallic reagents is reviewed. The article includes Suzuki–Miyaura, Kumada–Corriu, Negishi, and Hiyama cross-coupling reactions.1 Introduction2 Suzuki–Miyaura Cross-Coupling2.1 Palladium Catalysis2.2 Nickel Catalysis3 Kumada–Corriu Cross-Coupling3.1 Nickel Catalysis3.2 Iron Catalysis3.3 Cobalt Catalysis4 Negishi Cross-Coupling5 Hiyama Cross-Coupling6 Conclusion

Iron Catalysis in Target Synthesis

Synthesis ◽  
2020 ◽  
Vol 52 (07) ◽  
pp. 949-963
Author(s):  
Peter DaBell ◽  
Stephen P. Thomas
Keyword(s):  
Natural Products ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Total Syntheses ◽  
Iron Catalysis ◽  
Cross Coupling Reactions ◽  
Target Synthesis

The use of iron-catalysed organic transformations in the total syntheses of natural products has increased significantly. Iron-catalysed cross-coupling reactions are now widely applied in total syntheses and many other transformations, such as alkene functionalisation, oxidation, and cyclisation. The development of these processes, as well as many examples of their use in target synthesis, is presented here.1 Introduction2 Cross-Coupling Reactions3 Functionalisation of Unactivated Alkenes4 Carbocyclisation Reactions5 Oxidations6 Further Examples7 Conclusions

scholarly journals Arylhydrazines: novel and versatile electrophilic partners in cross-coupling reactions

RSC Advances ◽  
2018 ◽  
Vol 8 (59) ◽  
pp. 33828-33844 ◽  
Author(s):  
Akram Hosseinian ◽  
Robab Mohammadi ◽  
Sheida Ahmadi ◽  
Aazam Monfared ◽  
Zahra Rahmani
Keyword(s):  
Organic Chemistry ◽  
Cross Coupling ◽  
Biologically Active ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Valuable Compounds

Arylhydrazines are extremely valuable compounds in organic chemistry that are widely used for the synthesis of a variety of biologically active molecules such as indoles, indazoles, pyrazoles, aryltriazoles, β-lactams and quinazolines.

scholarly journals Decarboxylative cross-coupling reactions for P(O)–C bond formation

RSC Advances ◽  
2018 ◽  
Vol 8 (46) ◽  
pp. 26383-26398 ◽  
Author(s):  
Akram Hosseinian ◽  
Fatemeh Alsadat Hosseini Nasab ◽  
Sheida Ahmadi ◽  
Zahra Rahmani ◽  
Esmail Vessally
Keyword(s):  
Organic Chemistry ◽  
Organic Compounds ◽  
Medicinal Chemistry ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Materials Chemistry ◽  
Cross Coupling Reactions ◽  
Agricultural Chemistry ◽  
Phosphorus Containing

Phosphorus-containing compounds are one of the most important classes of organic compounds, which have wide applications in organic chemistry, medicinal chemistry, agricultural chemistry, and materials chemistry.

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