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

Formal Total Syntheses of Crocacin A-D

2005 ◽  
Vol 70 (10) ◽  
pp. 1696-1708 ◽  
Author(s):  
Magnus Besev ◽  
Christof Brehm ◽  
Alois Fürstner
Keyword(s):  
Natural Products ◽  
Aldol Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
The Common ◽  
Selective Addition

A concise route to the common polyketide fragment5of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features asyn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzedanti-selective addition of propargyl mesylate10to the chiral aldehyde9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

Cross-coupling reactions towards the synthesis of natural products

2021 ◽  
Author(s):  
Shaheera Tabassum ◽  
Ameer Fawad Zahoor ◽  
Sajjad Ahmad ◽  
Razia Noreen ◽  
Samreen Gul Khan ◽  
...  
Keyword(s):  
Natural Products ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

The Synthesis of Pharmaceuticals: The Effective Application of Secondary Boronic Esters in Enantioselective Suzuki ‐ Miyaura Cross ‐ Coupling Reactions

2016 ◽  
Author(s):  
Jonathon Moir
Keyword(s):  
Natural Products ◽  
Human Life ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Carbon Bonds ◽  
Effective Drugs

Pharmaceuticals and drugs have become an indispensable part of human life. Presently, a myriad of different drugs are available for a variety of mental and physical health concersn. The synthesis of these drugs, however, remains an elusive and often difficult aspect of the industry. The importance of chirality, or "handedness", in the synthesis of natural products is paramount, as any given pair of enantiomers can have widely differing physiological effects. As such, the ability to control the enantioselectivity of a reaction is of the utmost importance. One example of a facile method used to form carbon-carbon bonds is the Suzuki-Miyaura cross-coupling reaction. Not only is this reaction effective at coupling primary organoboronic esters with organohalides, but recent work in the Crudden group in the Department of Chemistry has revealed an effective method of also cross-couplingchiral secondary organoboronic esters with good retention of stereochemistry. This work, the first of its kind, is crucial in developing single-handed natural products for a wide array of applications, including applications in the pharmaceutical industry. The end result is safer and more effective drugs for distribution to the general public. To expand the scope of this project, new substrates are currently being synthesized for cross-coupling applications. The overall goal is to improve upon current methodologies, while helping to meet the industrial and academic needs of the future.  

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

scholarly journals Tris(acetylacetonato) Iron(III): Recent Developments and Synthetic Applications

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 161-177 ◽  
Author(s):  
Dennis Lübken ◽  
Marius Saxarra ◽  
Markus Kalesse
Keyword(s):  
Hydrogen Atom ◽  
Natural Product ◽  
Cross Coupling ◽  
Short Review ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Cross Coupling Reactions ◽  
Recent Developments

Tris(acetylacetonato) iron(III) [Fe(acac)3] is an indispensable reagent in synthetic chemistry. Its applications range from hydrogen atom transfer to cross-coupling reactions and to use as a Lewis acid. Consequently, the exceptional utility of Fe(acac)3 has been demonstrated in several total syntheses. This short review summarizes the applications of Fe(acac)3 in methodology and catalysis and highlights its use for the synthesis of medicinally relevant structures and in natural product syntheses.1 Introduction2 Hydrogen Atom Transfer (HAT)3 Oxidations and Radical Transformations4 Synthesis and Use of Alkynes and Allenes5 Cross-Couplings and Cycloisomerizations6 Borylations7 Miscellaneous Reactions8 Conclusions

scholarly journals Diaryl ethers synthesis: nano-catalysts in carbon-oxygen cross-coupling reactions

RSC Advances ◽  
2018 ◽  
Vol 8 (34) ◽  
pp. 19125-19143 ◽  
Author(s):  
Kamellia Nejati ◽  
Sheida Ahmadi ◽  
Mohammad Nikpassand ◽  
Parvaneh Delir Kheirollahi Nezhad ◽  
Esmail Vessally
Keyword(s):  
Natural Products ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Diaryl Ethers ◽  
Synthetic Drugs ◽  
Cross Coupling Reactions ◽  
Nano Catalysts

Diaryl ethers are found in natural products and synthetic drugs as well as in many pesticides and polymers.

On direct iron-catalyzed cross-coupling reactions

2010 ◽  
Vol 82 (7) ◽  
pp. 1545-1553 ◽  
Author(s):  
Waldemar Maximilian Czaplik ◽  
Matthias Mayer ◽  
Sabine Grupe ◽  
Axel Jacobi von Wangelin
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
One Pot ◽  
Iron Catalysis ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Direct Cross

A new methodology for the direct cross-coupling reaction between aryl halides and alkyl halides under iron catalysis is described. Unlike conventional protocols, the direct cross-coupling obviates the need for the preformation of stoichiometric amounts of Grignard species and thus exhibits a reduced hazard potential. The underlying one-pot reaction involves iron-catalyzed Grignard formation followed by a rapid cross-coupling step. Mechanistic data on the role of N,N,N',N'-tetramethylethylenediamine (TMEDA) as additive, the concentration of intermediates, and the nature of the catalyst species are discussed.

scholarly journals Acetylene in Organic Synthesis: Recent Progress and New Uses

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2442 ◽  
Author(s):  
Vladimir V. Voronin ◽  
Maria S. Ledovskaya ◽  
Alexander S. Bogachenkov ◽  
Konstantin S. Rodygin ◽  
Valentine P. Ananikov
Keyword(s):  
Recent Progress ◽  
Rapid Development ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Acetylene Molecule ◽  
Cross Coupling Reactions ◽  
Pharmaceutical Substances ◽  
Molecular Complexity ◽  
Different Levels

Recent progress in the leading synthetic applications of acetylene is discussed from the prospect of rapid development and novel opportunities. A diversity of reactions involving the acetylene molecule to carry out vinylation processes, cross-coupling reactions, synthesis of substituted alkynes, preparation of heterocycles and the construction of a number of functionalized molecules with different levels of molecular complexity were recently studied. Of particular importance is the utilization of acetylene in the synthesis of pharmaceutical substances and drugs. The increasing interest in acetylene and its involvement in organic transformations highlights a fascinating renaissance of this simplest alkyne molecule.

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