scholarly journals Bimetallic copper and zinc-catalyzed oxidative cycloaddition of 3-aminopyridazines and nitriles: a direct synthesis of 1,2,4-triazolo[1,5-b]pyridazines via C–N and N–N bond-forming process

RSC Advances ◽  
2017 ◽  
Vol 7 (59) ◽  
pp. 37208-37213 ◽  
Author(s):  
Qiu-Chao Mu ◽  
Ji-Yuan Lv ◽  
Mu-Yi Chen ◽  
Xing-Feng Bai ◽  
Jing Chen ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Bond Formation ◽  
N Addition ◽  
Forming Process ◽  
One Pot ◽  
Bond Forming ◽  
Copper And Zinc ◽  
Pyridazine Derivatives

One-pot formation of 1,2,4-triazolo[1,5-b]pyridazine derivatives is presented in this manuscript, in which the targets are offered via cooperative Cu(i)/Zn(ii)-catalyzed tandem C–N addition and I2/KI-mediated intramolecular N–N bond formation.

Microwave-accelerated Carbon-carbon and Carbon-heteroatom Bond Formation via Multi-component Reactions: A Brief Overview

2020 ◽  
Vol 7 (1) ◽  
pp. 23-39 ◽  
Author(s):  
Kantharaju Kamanna ◽  
Santosh Y. Khatavi
Keyword(s):  
Organic Synthesis ◽  
Bond Formation ◽  
Cycloaddition Reaction ◽  
Nanoparticle Synthesis ◽  
Single Step ◽  
Bioactive Molecules ◽  
One Pot ◽  
Bond Forming ◽  
Material Interest ◽  
Carbon Carbon Bond

Multi-Component Reactions (MCRs) have emerged as an excellent tool in organic chemistry for the synthesis of various bioactive molecules. Among these, one-pot MCRs are included, in which organic reactants react with domino in a single-step process. This has become an alternative platform for the organic chemists, because of their simple operation, less purification methods, no side product and faster reaction time. One of the important applications of the MCRs can be drawn in carbon- carbon (C-C) and carbon-heteroatom (C-X; X = N, O, S) bond formation, which is extensively used by the organic chemists to generate bioactive or useful material synthesis. Some of the key carbon- carbon bond forming reactions are Grignard, Wittig, Enolate alkylation, Aldol, Claisen condensation, Michael and more organic reactions. Alternatively, carbon-heteroatoms containing C-N, C-O, and C-S bond are also found more important and present in various heterocyclic compounds, which are of biological, pharmaceutical, and material interest. Thus, there is a clear scope for the discovery and development of cleaner reaction, faster reaction rate, atom economy and efficient one-pot synthesis for sustainable production of diverse and structurally complex organic molecules. Reactions that required hours to run completely in a conventional method can now be carried out within minutes. Thus, the application of microwave (MW) radiation in organic synthesis has become more promising considerable amount in resource-friendly and eco-friendly processes. The technique of microwaveassisted organic synthesis (MAOS) has successfully been employed in various material syntheses, such as transition metal-catalyzed cross-coupling, dipolar cycloaddition reaction, biomolecule synthesis, polymer formation, and the nanoparticle synthesis. The application of the microwave-technique in carbon-carbon and carbon-heteroatom bond formations via MCRs with major reported literature examples are discussed in this review.

Copper nanoparticles supported on charcoal mediated one-pot three-component synthesis of N-substituted-2H-indazoles via consecutive condensation C–N and N–N bond formation

2019 ◽  
Vol 97 (4) ◽  
pp. 303-309 ◽  
Author(s):  
Reza Khalifeh ◽  
Faranak Karimzadeh
Keyword(s):  
Copper Nanoparticles ◽  
Sodium Azide ◽  
Direct Synthesis ◽  
Bond Formation ◽  
Primary Amines ◽  
Title Reaction ◽  
One Pot

An efficient and straightforward protocol for direct synthesis of 2H-indazoles is achieved from consecutive condensation of 2-halobenzaldehydes, primary amines, and sodium azide catalyzed by heterogeneous copper nanoparticles on charcoal (Cu/C) is achieved. The recoverable heterogeneous copper nanoparticles on charcoal (Cu/C) catalyst exhibited an impressive activity for the title reaction without any additives (expensive ligands, etc.). A series of structurally diverse 2H-indazoles were prepared in good to excellent yields from easily accessible starting materials by employing this protocol.

Transition-Metal-Catalyzed Annulative Coupling Cascade for the Synthesis of 3-Methyleneisoindolin-1-ones

Synthesis ◽  
2020 ◽  
Vol 52 (06) ◽  
pp. 807-818 ◽  
Author(s):  
So Won Youn
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Short Review ◽  
Coupling Reactions ◽  
Cyclization Reactions ◽  
One Pot ◽  
Bond Forming ◽  
Wide Range ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This short review describes the recent progress made on transition-metal-catalyzed annulative couplings for the synthesis of 3-methyleneisoindolin-1-ones, which are useful intermediates for the synthesis of numerous alkaloids and can be often found in a wide range of natural products and pharmaceuticals. In particular, new one-pot multiple C–C/C–N bond-forming processes for the construction of the 5-methylenepyrrol-2-one nucleus of such compounds are summarized.1 Introduction2 Intramolecular Cyclization Reactions: C3–N or C3–C3a and C–C Bond Formation3 Intermolecular Annulative Coupling Reactions3.1 C3–C3a and C3–N Bond Formation3.2 C1–C7a and C3–N Bond Formation3.3 C1–C7a and C1–N Bond Formation3.4 C1–C7a, C1–N and C3–N Bond Formation3.5 C3–C3a, C1–C7a, C1–N and C3–N Bond Formation: A Pd-Catalyzed One-Pot Sonogashira Coupling–Carbonylation–Amination–Cyclization Cascade4 Conclusion

One-pot two-step synthesis of N-arylcarbazole-based skeleton

RSC Advances ◽  
2016 ◽  
Vol 6 (49) ◽  
pp. 43250-43260 ◽  
Author(s):  
Sheng Tao ◽  
Ning Liu ◽  
Bin Dai
Keyword(s):  
Forming Process ◽  
One Pot ◽  
Bond Forming ◽  
Site Selective

A highly site-selective, one-pot, sequential C–N and C–C bond forming process was developed, affording a carbazole-based skeleton that contains biphenyl and diarylacetylene cores.

Radical Capture at Ni(II) Complexes: C-C, C-N, and C-O Bond Formation

2019 ◽  
Author(s):  
Abolghasem (Gus) Bakhoda ◽  
Stefan Wiese ◽  
Christine Greene ◽  
Bryan C. Figula ◽  
Jeffery A. Bertke ◽  
...  
Keyword(s):  
Functional Groups ◽  
Bond Formation ◽  
Dft Studies ◽  
Bond Forming ◽  
Aryl Amines ◽  
Shed Light ◽  
Competing Pathways

<p>The dinuclear b-diketiminato Ni<sup>II</sup><i>tert</i>-butoxide {[Me<sub>3</sub>NN]Ni}<sub>2</sub>(<i>μ</i>-O<i><sup>t</sup></i>Bu)<sub>2 </sub>(<b>2</b>), synthesized from [Me<sub>3</sub>NN]Ni(2,4-lutidine) (<b>1</b>) and di-<i>tert</i>-butylperoxide, is a versatile precursor for the synthesis of a series of Ni<sup>II</sup>complexes [Me<sub>3</sub>NN]Ni-FG to illustrate C-C, C-N, and C-O bond formation at Ni<sup>II </sup>via radicals. {[Me<sub>3</sub>NN]Ni}<sub>2</sub>(<i>μ</i>-O<i><sup>t</sup></i>Bu)<sub>2 </sub>reacts with nitromethane, alkyl and aryl amines, acetophenone, benzamide, ammonia and phenols to deliver corresponding mono- or dinuclear [Me<sub>3</sub>NN]Ni-FG species (FG = O<sub>2</sub>NCH<sub>2</sub>, R-NH, ArNH, PhC(O)NH, PhC(O)CH<sub>2</sub>, NH<sub>2</sub>and OAr). Many of these Ni<sup>II </sup>complexes are capable of capturing the benzylic radical PhCH(•)CH<sub>3 </sub>to deliver corresponding PhCH(FG)CH<sub>3 </sub>products featuring C-C, C-N or C-O bonds. DFT studies shed light on the mechanism of these transformations and suggest two competing pathways that depend on the nature of the functional groups. These radical capture reactions at [Ni<sup>II</sup>]-FG complexes outline key C-C, C-N, and C-O bond forming steps and suggest new families of nickel radical relay catalysts.</p>

Metal-Free Photoredox-Catalyzed C–H/C–H Coupling of Arenes Enabled by Interrupted Pummerer Activation

2019 ◽  
Author(s):  
Miles Aukland ◽  
Mindaugas Šiaučiulis ◽  
Adam West ◽  
Gregory Perry ◽  
David Procter
Keyword(s):  
Natural Product ◽  
Selective Reduction ◽  
Cross Coupling ◽  
One Pot ◽  
Complex Molecules ◽  
Pummerer Reaction ◽  
Metal Free ◽  
Bond Forming ◽  
Coupling Partner ◽  
Bioactive Natural Product

<p>Aryl–aryl cross-coupling constitutes one of the most widely used procedures for the synthesis of high-value materials, ranging from pharmaceuticals to organic electronics and conducting polymers. The assembly of (hetero)biaryl scaffolds generally requires multiple steps; coupling partners must be functionalized before the key bond-forming event is considered. Thus, the development of selective C–H arylation processes in arenes, that side-step the need for prefunctionalized partners, is crucial for streamlining the construction of these key architectures. Here we report an expedient, one-pot assembly of (hetero)biaryl motifs using photocatalysis and two non-prefunctionalized arene partners. The approach is underpinned by the activation of a C–H bond in an arene coupling partner using the interrupted Pummerer reaction. A unique pairing of the organic photoredox catalyst and the intermediate dibenzothiophenium salts enables highly selective reduction in the presence of sensitive functionalities. The utility of the metal-free, one-pot strategy is exemplified by the synthesis of a bioactive natural product and the modification of complex molecules of societal importance.</p>

Recent Advances on C-Se Bond-forming Reactions at Low and Room Temperature

2020 ◽  
Vol 23 (28) ◽  
pp. 3206-3225 ◽  
Author(s):  
Amol D. Sonawane ◽  
Mamoru Koketsu
Keyword(s):  
Room Temperature ◽  
Bond Formation ◽  
Bond Forming ◽  
Material Chemistry ◽  
Recent Advances ◽  
Bond Forming Reactions ◽  
Bond Formation Reactions

: Over the last decades, many methods have been reported for the synthesis of selenium- heterocyclic scaffolds because of their interesting reactivities and applications in the medicinal as well as in the material chemistry. This review describes the recent numerous useful methodologies on C-Se bond formation reactions which were basically carried out at low and room temperature.

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