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 Sequential In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reactions using bromopropargyl aryl ethers and amines

2017 ◽  
Vol 4 (4) ◽  
pp. 500-505 ◽  
Author(s):  
Lorena Alonso-Marañón ◽  
Luis A. Sarandeses ◽  
M. Montserrat Martínez ◽  
José Pérez Sestelo
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
One Pot ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Aryl Ethers

A sequential one-pot In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reaction using bromopropargyl aryl ethers and amines has been developed.

scholarly journals Copper-Promoted One-Pot Approach: Synthesis of Benzimidazoles

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1788
Author(s):  
S. N. Murthy Boddapati ◽  
Ramana Tamminana ◽  
Ravi Kumar Gollapudi ◽  
Sharmila Nurbasha ◽  
Mohamed E. Assal ◽  
...  
Keyword(s):  
Copper Catalyst ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
One Pot ◽  
Catalytic Systems ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Substrate Tolerance ◽  
High Yields

A facile, one-pot, and proficient method was developed for the production of various 2-arylaminobenzimidazoles. This methodology is based for the first time on a copper catalyst promoted domino C–N cross-coupling reaction for the generation of 2-arylaminobenzimidazoles. Mechanistic investigations revealed that the synthetic pathway involves a copper-based desulphurization/nucleophilic substitution and a subsequent domino intra and intermolecular C–N cross-coupling reactions. Some of the issues typically encountered during the synthesis of 2-arylaminobezimidazoles, including the use of expensive catalytic systems and the low reactivity of bromo precursors, were addressed using this newly developed copper-catalyzed method. The reaction procedure is simple, generally with excellent substrate tolerance, and provides good to high yields of the desired products.

Enhanced catalytic performance of Pd–Pt nanodendrites for ligand-free Suzuki cross-coupling reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (36) ◽  
pp. 28467-28473 ◽  
Author(s):  
Zheng-Jun Wang ◽  
Jing-Jing Lv ◽  
Jiu-Ju Feng ◽  
Ningbo Li ◽  
Xinhua Xu ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Catalytic Performance ◽  
Coupling Reactions ◽  
Wet Chemical Method ◽  
One Pot ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Ligand Free ◽  
Wet Chemical

The Pd–Pt NDs were synthesized by a one-pot wet-chemical method, which showed enhanced catalytic activity toward Suzuki cross-coupling reaction.

scholarly journals Cross-coupling Reactions of Monosubstituted Tetrazines

2021 ◽  
Author(s):  
Lukas Hoff ◽  
Simon Schnell ◽  
Andrea Tomio ◽  
Anthony Linden ◽  
Karl Gademann
Keyword(s):  
High Temperatures ◽  
Catalytic System ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Direct Cross ◽  
Optimized Conditions ◽  
Powerful Strategy

<div><div><div><p>A fast and mild method for the Pd-catalyzed cross-coupling reaction of monosubstituted 3-bromo-1,2,4,5-tetrazine is presented. Investigation of silver-based additives revealed that Ag2CO3 is the optimal mediator, enabling the process without the need for strong bases or high temperatures. Electronic modification of the classical 1,1′- bis(diphenylphosphine)ferrocene (dppf) ligand proved to be a powerful strategy in tailoring the catalytic system to the requirements set by the process. Under the optimized conditions a scope comprising a variety of alkyl-, heteroatom-, and halide substituted aryl- and heteroaryl-tetrazines were prepared in good to excellent yields (29 examples, up to 87% yield). This method constitutes the first example of a direct cross-coupling reaction of monosubstituted tetrazines.</p></div></div></div>

Sulfides Synthesis: Nanocatalysts in C–S Cross-Coupling Reactions

2016 ◽  
Vol 69 (6) ◽  
pp. 585 ◽  
Author(s):  
Lotfi Shiri ◽  
Arash Ghorbani-Choghamarani ◽  
Mosstafa Kazemi
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Copper Ferrite ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Synthetic Transformation ◽  
Cross Coupling Reaction ◽  
Wide Range ◽  
Points Of View

The C–S cross-coupling reaction of aryl halides with thiols or sulfur sources is a key and valuable synthetic transformation in chemistry and medicine as well as in biology, and the development of novel efficient synthetic protocols for the synthesis of the corresponding products (sulfides) is highly desired. Among a wide range of catalysts used in C–S coupling reactions, metallic nanocatalysts have attracted notable interest. Herein, we summarize recent breakthroughs in the arena of metal nanocatalysts employed in C–S cross-coupling reactions with the goal of stimulating further progress in this field. This review is divided into three main sections according to the nature of the metal nanocatalysts discussed. The first section focuses on naked or purely metallic catalysts in nano-size, such as Cu, Pd, Ni, and In. The second section focuses on the role of Fe3O4 magnetic nanoparticles and mesoporous silica nanomaterials, such as MCM-41 and SBA-15, as catalyst supports. Finally, the third section focuses on the catalytic activities of copper ferrite nanoparticles in C–S cross-coupling reactions. Additionally, the recovery and reusability of the nanocatalyst, which are very important from commercial and economical points of view, are comprehensively discussed in this review.

scholarly journals Cross-coupling Reactions of Monosubstituted Tetrazines

2021 ◽  
Author(s):  
Lukas Hoff ◽  
Simon Schnell ◽  
Andrea Tomio ◽  
Anthony Linden ◽  
Karl Gademann
Keyword(s):  
High Temperatures ◽  
Catalytic System ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Direct Cross ◽  
Optimized Conditions ◽  
Powerful Strategy

<div><div><div><p>A fast and mild method for the Pd-catalyzed cross-coupling reaction of monosubstituted 3-bromo-1,2,4,5-tetrazine is presented. Investigation of silver-based additives revealed that Ag2CO3 is the optimal mediator, enabling the process without the need for strong bases or high temperatures. Electronic modification of the classical 1,1′- bis(diphenylphosphine)ferrocene (dppf) ligand proved to be a powerful strategy in tailoring the catalytic system to the requirements set by the process. Under the optimized conditions a scope comprising a variety of alkyl-, heteroatom-, and halide substituted aryl- and heteroaryl-tetrazines were prepared in good to excellent yields (29 examples, up to 87% yield). This method constitutes the first example of a direct cross-coupling reaction of monosubstituted tetrazines.</p></div></div></div>

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

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.  

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

scholarly journals Synthesis of 4-Alkyl-4H-1,2,4-triazole Derivatives by Suzuki Cross-coupling Reactions and Their Luminescence Properties

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 652 ◽  
Author(s):  
Monika Olesiejuk ◽  
Agnieszka Kudelko ◽  
Marcin Swiatkowski ◽  
Rafal Kruszynski
Keyword(s):  
Ionic Liquids ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Luminescence Properties ◽  
Coupling Reactions ◽  
Triazole Derivatives ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Derivatives Of

New derivatives of 4-alkyl-3,5-diaryl-4H-1,2,4-triazole were synthesized utilizing the Suzuki cross-coupling reaction. The presented methodology comprises of the preparation of bromine-containing 4-alkyl-4H-1,2,4-triazoles and their coupling with different commercially available boronic acids in the presence of ionic liquids or in conventional solvents. The obtained compounds were tested for their luminescence properties.

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