Mercury in organic chemistry. 22. Carbon-carbon bond formation via organocopper-organomercury cross-coupling reactions

1982 ◽  
Vol 1 (1) ◽  
pp. 74-81 ◽  
Author(s):  
Richard C. Larock ◽  
Douglas R. Leach
Keyword(s):  
Organic Chemistry ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Carbon Bond ◽  
Cross Coupling Reactions ◽  
Carbon Carbon 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.

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

Synthesis of Benzamide Derivatives by the Reaction of Arenes and Isocyanides through a C–H Bond Activation Strategy

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 94-98 ◽  
Author(s):  
Mehdi Khalaj ◽  
Mahboubeh Taherkhani ◽  
Seyed Mousavi-Safavi ◽  
Jafar Akbari
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Benzene Derivatives ◽  
Formation Reaction ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Benzamide Derivatives

A carbon–carbon bond formation reaction between isocyanides and benzene derivatives is reported. In contrast to traditional cross-coupling reactions, which require aryl halides or pseudohalides, we use a palladium catalyst to generate the aryl–palladium through C–H bond activation of arenes. This method offers an attractive approach to a range of benzamides from readily accessible benzene derivatives.

Ferromagnetic α-Fe2O3 NPs: a potential catalyst in Sonogashira–Hagihara cross coupling and hetero-Diels–Alder reactions

2016 ◽  
Vol 18 (6) ◽  
pp. 1495-1505 ◽  
Author(s):  
Meenal Kataria ◽  
Subhamay Pramanik ◽  
Navleen Kaur ◽  
Manoj Kumar ◽  
Vandana Bhalla
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Diels Alder ◽  
Recyclable Catalyst ◽  
Coupling Reactions ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Applications of in situ generated ferromagnetic α-Fe2O3 NPs as an efficient and recyclable catalyst for carbon–carbon bond formation via Sonogashira–Hagihara coupling reactions and the synthesis of pyran derivatives by hetero-Diels–Alder reactions have been demonstrated.

An efficient mesoporous carbon nitride (g-C3N4) functionalized Pd catalyst for carbon–carbon bond formation reactions

RSC Advances ◽  
2016 ◽  
Vol 6 (55) ◽  
pp. 49376-49386 ◽  
Author(s):  
S. Elavarasan ◽  
B. Baskar ◽  
C. Senthil ◽  
Piyali Bhanja ◽  
A. Bhaumik ◽  
...  
Keyword(s):  
Mesoporous Carbon ◽  
Carbon Nitride ◽  
Bond Formation ◽  
Cross Coupling ◽  
Pd Nanoparticles ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Mesoporous Carbon Nitride ◽  
Efficient Heterogeneous Catalyst

Pd-nanoparticles on mesoporous nitrogen-rich carbon nitride (MCN) serves as an efficient heterogeneous catalyst for Sonogashira cross-coupling reactions.

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 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.

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