Linear Heterocyclic Aromatic Fluorescence Compounds Having Various Donor–Acceptor Spacers Prepared by the Combination of Carbon–Carbon Bond and Carbon–Nitrogen Bond Cross-Coupling Reactions

2011 ◽  
Vol 76 (11) ◽  
pp. 4444-4456 ◽  
Author(s):  
Bin Hu ◽  
Shu-Jun Fu ◽  
Feng Xu ◽  
Tao Tao ◽  
Hao-Yu Zhu ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Carbon Bond ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Donor Acceptor ◽  
Nitrogen Bond

scholarly journals Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

2016 ◽  
Vol 12 ◽  
pp. 2898-2905 ◽  
Author(s):  
Michal Medvecký ◽  
Igor Linder ◽  
Luise Schefzig ◽  
Hans-Ulrich Reissig ◽  
Reinhold Zimmer
Keyword(s):  
Click Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
High Efficacy ◽  
Carbon Bond ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed ◽  
Oxazine Derivatives

Iodination of carbohydrate-derived 3,6-dihydro-2H-1,2-oxazines of type 3 using iodine and pyridine in DMF furnished 5-iodo-substituted 1,2-oxazine derivatives 4 with high efficacy. The alkenyl iodide moiety of 1,2-oxazine derivatives syn-4 and anti-4 was subsequently exploited for the introduction of new functionalities at the C-5 position by applying palladium-catalyzed carbon–carbon bond-forming reactions such as Sonogashira, Heck, or Suzuki coupling reactions as well as a cyanation reaction. These cross-coupling reactions led to a series of 5-alkynyl-, 5-alkenyl-, 5-aryl- and 5-cyano-substituted 1,2-oxazine derivatives being of considerable interest for further synthetic elaborations. This was exemplarily demonstrated by the hydrogenation of syn-21 and anti-24 and by a click reaction of a 5-alkynyl-substituted precursor.

scholarly journals Microwave-Assisted Palladium-Catalyzed Cross-Coupling Reactions: Generation of Carbon–Carbon Bond

Catalysts ◽  
2019 ◽  
Vol 10 (1) ◽  
pp. 4 ◽  
Author(s):  
Kifah S. M. Salih ◽  
Younis Baqi
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Microwave Technology ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Microwave Assisted ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Challenging Tasks ◽  
Palladium Catalyzed

Cross-coupling reactions furnishing carbon–carbon (C–C) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Negishi, Heck, Kumada, Sonogashira, Stille, Suzuki, and Hiyama, utilizing palladium or its salts as catalysis have, for decades, attracted and inspired researchers affiliated with academia and industry. Tremendous efforts have been paid to develop and achieve more sustainable reaction conditions, such as the reduction in energy consumption by applying the microwave irradiation technique. Chemical reactions under controlled microwave conditions dramatically reduce the reaction time and therefore resulting in increase in the yield of the desired product by minimizing the formation of side products. In this review, we mainly focus on the recent advances and applications of palladium catalyzed cross-coupling carbon–carbon bond formation under microwave technology.

Transition-metal-catalyzed carbon-carbon bond forming reactions: regio- and chemoselective iron(0)-catalyzed diene to olefin cross-coupling reactions

1986 ◽  
Vol 5 (11) ◽  
pp. 2395-2398 ◽  
Author(s):  
James M. Takacs ◽  
Lawrence G. Anderson ◽  
G. V. Bindu. Madhavan ◽  
Mark W. Creswell ◽  
Franklin L. Seely ◽  
...  
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Carbon Bond ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Cu(III)-Mediated Aerobic Oxidations

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 334-358 ◽  
Author(s):  
Jean-Philip Lumb ◽  
Kenneth Esguerra
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Oxidation Reactions ◽  
General Introduction ◽  
Model Complexes ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Type 3

CuIII species have been invoked in many copper-catalyzed transformations including cross-coupling reactions and oxidation reactions. In this review, we will discuss seminal discoveries that have advanced our understanding of the CuI/CuIII redox cycle in the context of C–C and C–heteroatom aerobic cross-coupling reactions, as well as C–H oxidation reactions mediated by CuIII–dioxygen adducts.1 General Introduction2 Early Examples of CuIII Complexes3 Aerobic CuIII-Mediated Carbon–Heteroatom Bond-Forming Reactions4 Aerobic CuIII-Mediated Carbon–Carbon Bond-Forming Reactions5 Bioinorganic Studies of CuIII Complexes from CuI and O2 5.1 O2 Activation5.2 Biomimetic CuIII Complexes from CuI and Dioxygen5.2.1 Type-3 Copper Enzymes and Dinuclear Cu Model Complexes5.2.2 Particulate Methane Monooxygenase and Di- and Trinuclear Cu Model Complexes5.2.3 Dopamine–β-Monooxygenase and Mononuclear Cu Model Complexes6 Conclusion

Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 267-278
Author(s):  
Kenneth M. Nicholas ◽  
Chandrasekhar Bandari
Keyword(s):  
Transition Metal ◽  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Transition Metal Catalysts ◽  
Coupling Reactions ◽  
Reductive Coupling ◽  
Practical Applications ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond

AbstractThe prospective utilization of abundant, CO2-neutral, renewable feedstocks is driving the discovery and development of new reactions that refunctionalize oxygen-rich substrates such as alcohols and polyols through C–O bond activation. In this review, we highlight the development of transition-metal-promoted reactions of renewable alcohols and epoxides that result in carbon–carbon bond-formation. These include reductive self-coupling reactions and cross-coupling reactions of alcohols with alkenes and arene derivatives. Early approaches to reductive couplings employed stoichiometric amounts of low-valent transition-metal reagents to form the corresponding hydrocarbon dimers. More recently, the use of redox-active transition-metal catalysts together with a reductant has enhanced the practical applications and scope of the reductive coupling of alcohols. Inclusion of other reaction partners with alcohols such as unsaturated hydrocarbons and main-group organometallics has further expanded the diversity of carbon skeletons accessible and the potential for applications in chemical synthesis. Catalytic reductive coupling and cross-coupling reactions of epoxides are also highlighted. Mechanistic insights into the means of C–O activation and C–C bond formation, where available, are also highlighted.1 Introduction2 Stoichiometric Reductive Coupling of Alcohols3 Catalytic Reductive Coupling of Alcohols3.1 Heterogeneous Catalysis3.2 Homogeneous Catalysis4 Reductive Cross-Coupling of Alcohols4.1 Reductive Alkylation4.2 Reductive Addition to Olefins5 Epoxide Reductive Coupling Reactions6 Conclusions and Future Directions

scholarly journals Heterogeneous catalysis by ultra-small bimetallic nanoparticles surpassing homogeneous catalysis for carbon–carbon bond forming reactions

Nanoscale ◽  
2020 ◽  
Vol 12 (37) ◽  
pp. 19191-19202 ◽  
Author(s):  
Nazgol Norouzi ◽  
Mrinmoy K. Das ◽  
Alexander J. Richard ◽  
Amr A. Ibrahim ◽  
Hani M. El-Kaderi ◽  
...  
Keyword(s):  
Heterogeneous Catalysis ◽  
Homogeneous Catalysis ◽  
Bimetallic Catalysts ◽  
Fumed Silica ◽  
Bimetallic Nanoparticles ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond

Heterogeneous Pd-based bimetallic catalysts supported on fumed silica with high activity and selectivity matching those of homogeneous catalysts have been developed for carbon–carbon cross-coupling reactions.

scholarly journals New Trends in C–C Cross-Coupling Reactions: The Use of Unconventional Conditions

Molecules ◽  
2020 ◽  
Vol 25 (23) ◽  
pp. 5506
Author(s):  
Marta A. Andrade ◽  
Luísa M. D. R. S. Martins
Keyword(s):  
Alternative Energy ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Energy Sources ◽  
Coupling Reactions ◽  
Alternative Energy Sources ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Cross Coupling Reaction ◽  
Efficiency And Effectiveness

The ever-growing interest in the cross-coupling reaction and its applications has increased exponentially in the last decade, owing to its efficiency and effectiveness. Transition metal-mediated cross-couplings reactions, such as Suzuki–Miyaura, Sonogashira, Heck, and others, are powerful tools for carbon–carbon bond formations and have become truly fundamental routes in catalysis, among other fields. Various greener strategies have emerged in recent years, given the widespread popularity of these important reactions. The present review comprises literature from 2015 onward covering the implementation of unconventional methodologies in carbon–carbon (C–C) cross-coupling reactions that embodies a variety of strategies, from the use of alternative energy sources to solvent- free and green media protocols.

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