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.

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The article has been withdrawn at the request of editor of the journal Current Organic Chemistry: Bentham Science apologizes to the readers of the journal for any inconvenience this may have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.

scholarly journals Biocatalytic oxidative cross-coupling reactions for biaryl bond formation

2021 ◽  
Author(s):  
Lara Zetzsche ◽  
Jessica Yazarians ◽  
Suman Chakrabarty ◽  
Meagan Hinze ◽  
April Lukowski ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Bond Formation ◽  
Cross Coupling ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Cytochrome P450 Enzymes ◽  
Cross Coupling Reactions ◽  
Site Selectivity ◽  
Valuable Compounds ◽  
Selective Process

Despite their varied purposes, many indispensable molecules in medicine, materials, and asymmetric catalysis share a biaryl core. The necessity of joining arene building blocks to access these valuable compounds has inspired multiple approaches for biaryl bond formation and challenged chemists to develop increasingly concise and robust methods for this task. Oxidative coupling of two C–H bonds offers an efficient strategy for the formation of a biaryl C–C bond, however, fundamental challenges remain in controlling the reactivity and selectivity for uniting a given pair of substrates. Biocatalytic oxidative cross-coupling reactions have the potential to overcome limitations inherent to small molecule- mediated methods by providing a paradigm with catalyst-controlled selectivity. In this article, we disclose a strategy for biocatalytic cross-coupling through oxidative C–C bond formation using cytochrome P450 enzymes. We demonstrate the ability to catalyze cross-coupling reactions on a panel of phenolic substrates using natural P450 catalysts. Moreover, we engineer a P450 to possess the desired reactivity, site- selectivity, and atroposelectivity by transforming a low-yielding, unselective reaction into a highly efficient and selective process. This streamlined method for constructing sterically hindered biaryl bonds provides a programmable platform for assembling molecules with catalyst-controlled reactivity and selectivity.

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.

Transition-Metal-Catalyzed Cross-Coupling Reactions of Grignard Reagents

Synthesis ◽  
2020 ◽  
Author(s):  
Zoltán Hell ◽  
Kinga Juhász ◽  
Ágnes Magyar
Keyword(s):  
Transition Metal ◽  
Transition Metals ◽  
Cross Coupling ◽  
Biologically Active ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Nickel Catalysis ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractTransition-metal-catalyzed cross-coupling of organo­halides, ethers, sulfides, amines, and alcohols (and derivatives thereof) with Grignard reagents, known as the Kumada–Tamao–Corriu reaction, can be used to prepare important intermediates in the synthesis of numerous­ biologically active compounds. The most frequently used transition metals are nickel, palladium, and iron, but there are several examples for cross-coupling reactions catalyzed by copper, cobalt, manganese, chromium, etc. salts and complexes. The aim of this review is to summarize the most important transition-metal-catalyzed cross-coupling reactions realized in the period 2000 to 2020.1 Introduction2 Nickel Catalysis3 Palladium Catalysis4 Iron Catalysis5 Catalysis by Other Transition Metals5.1 Cobalt Catalysis5.2 Copper Catalysis5.3 Manganese Catalysis5.4 Chromium Catalysis6 Conclusion

scholarly journals Tertiary Enamides as Versatile and Valuable Substrates to Reach Chemical Diversity

Synthesis ◽  
2020 ◽  
Vol 52 (17) ◽  
pp. 2497-2511 ◽  
Author(s):  
Laurence Miesch ◽  
Frédéric Beltran
Keyword(s):  
Cross Coupling ◽  
Chemical Diversity ◽  
Biologically Active ◽  
Coupling Reactions ◽  
Great Stability ◽  
New Methods ◽  
Sigmatropic Rearrangements ◽  
Cross Coupling Reactions ◽  
Nitrogen Containing Compounds ◽  
Made In

Tertiary enamides display versatile reactivity and great stability compared to their enamine congeners. This review covers progress made in the development of new methods involving the enaminic reactivity of tertiary enamides with respect to the synthesis of complex nitrogen-containing compounds. A focus on the preparation of biologically active molecules is also presented. The syntheses reported herein are classified based on their reaction type. In addition, mechanistic insights are given for most of the new transformations.1 Introduction2 [2+2] Cycloadditions3 [4+2] Cycloadditions4 Electrocyclizations and Cycloisomerizations5 Sigmatropic Rearrangements6 Nucleophilic Additions7 Tertiary Enamides as Electrophiles8 Cross-Coupling Reactions9 Tertiary-Enamide-Assisted Reactions10 Conclusion and Perspectives

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.

scholarly journals Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Chlorobenzenesulfonates

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5895
Author(s):  
Elwira Bisz
Keyword(s):  
Organic Chemistry ◽  
Catalytic System ◽  
Cross Coupling ◽  
Environmentally Benign ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions ◽  
Bioactive Properties ◽  
Synthetic Intermediates

Aryl sulfonate esters are versatile synthetic intermediates in organic chemistry as well as attractive architectures due to their bioactive properties. Herein, we report the synthesis of alkyl-substituted benzenesulfonate esters by iron-catalyzed C(sp2)–C(sp3) cross-coupling of Grignard reagents with aryl chlorides. The method operates using an environmentally benign and sustainable iron catalytic system, employing benign urea ligands. A broad range of chlorobenzenesulfonates as well as challenging alkyl organometallics containing β-hydrogens are compatible with these conditions, affording alkylated products in high to excellent yields. The study reveals that aryl sulfonate esters are the most reactive activating groups for iron-catalyzed alkylative C(sp2)–C(sp3) cross-coupling of aryl chlorides with Grignard reagents.

scholarly journals Recent developments in decarboxylative cross-coupling reactions between carboxylic acids and N–H compounds

RSC Advances ◽  
2019 ◽  
Vol 9 (16) ◽  
pp. 8964-8976 ◽  
Author(s):  
Sattar Arshadi ◽  
Saeideh Ebrahimiasl ◽  
Akram Hosseinian ◽  
Aazam Monfared ◽  
Esmail Vessally
Keyword(s):  
Organic Chemistry ◽  
Carboxylic Acids ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Structural Variety ◽  
Cross Coupling Reactions ◽  
Recent Developments

Carboxylic acids and their derivatives are ubiquitous compounds in organic chemistry, and are widely commercially available in a large structural variety.

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