Palladium-Catalyzed Copper-Promoted Hiyama-Type Carbon–­Carbon Cross-Coupling Reactions of Dihetaryl Disulfides as ­Electrophiles

Synlett ◽  
2017 ◽  
Vol 29 (03) ◽  
pp. 330-335 ◽  
Author(s):  
Zheng-Jun Quan ◽  
Xi-Cun Wang ◽  
Ming-Xia Liu ◽  
Hai-Peng Gong
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
High Reactivity ◽  
Attractive Alternative ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

Dihetaryl disulfides were used as electrophiles in a palladium-catalyzed carbon–carbon cross-coupling reaction with arylsilanes to ­realize a Hiyama-type reaction. This unique transformation shows high reactivity, excellent functional-group tolerance, and mild reaction conditions, making it an attractive alternative to conventional cross-coupling approaches for carbon−carbon bond construction.

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 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.

scholarly journals Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

2012 ◽  
Vol 8 ◽  
pp. 2004-2018 ◽  
Author(s):  
Rajendra Surasani ◽  
Dipak Kalita ◽  
A V Dhanunjaya Rao ◽  
K B Chandrasekhar
Keyword(s):  
Amino Acid ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Amino Acid Esters ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Acid Esters

Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs2CO3, dioxane and palladium catalyst precursors Pd(OAc)2/Pd2(dba)3. The combination of Pd(OAc)2, Xantphos, K2CO3 and dioxane was found to be crucial for the C–O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives.

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.

scholarly journals 2-(3-Cyanopropyldimethylsilyl)ethyl as a Polar Sulfur Protecting Group

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4153-4164
Author(s):  
Linda M. Bannwart ◽  
Pascal S. Rieder ◽  
Marcel Mayor
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Thiol Group ◽  
Organosulfur Compounds ◽  
Coupling Reactions ◽  
Protecting Group ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
The Stability

Organosulfur compounds are ubiquitous in synthetic chemistry, biology and materials chemistry. The reactivity of free sulfhydryls requires their masking in many synthetic strategies. To facilitate the isolation of protected thiols by chromatography, we propose 2-(3-cyanopropyldimethylsilyl)ethyl as a polar protecting group analogue of 2-(trimethylsilyl)ethyl. The masked thiophenol is obtained in two synthetically complementing ways. Either an existing thiophenol is protected, or the protected thiol group is introduced by a cross-coupling reaction. In both cases the required reagents are readily available from inexpensive starting materials. Thiol protection and thiol introduction both tolerate a large variety of functional groups and substitution patterns, and the protected thiophenols are stable toward a broad range of reaction conditions. The stability of the protected derivatives in cross-coupling reactions and the mild reaction conditions for the release of the protecting group further emphasizes the potential of the methodology.

scholarly journals Highly efficient synthesis of 2-substituted benzo[b]furan derivatives from the cross-coupling reactions of 2-halobenzo[b]furans with organoalane reagents

Synthesis ◽  
2021 ◽  
Author(s):  
chang wen ◽  
Qing Han Li ◽  
Chuan Wu ◽  
ruiqiang Luo ◽  
Feng Chen
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Practical Method ◽  
Bioactive Molecules ◽  
Coupling Reactions ◽  
Highly Efficient ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
The Cross

A highly efficient and simple route for the synthesis of 2-substituted benzo[b]furans has been developed by Palladium catalyzed the cross-coupling reaction of 2-halobenzo[b]furans with aryl, alkynyl and alkylaluminum reagents. Various 2-aryl, 2-alkynyl and 2-alkyl substituted benzo[b]furans derivatives can be obtained with 23-97% isolated yields using 2-3 mol% PdCl2/ 4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[b]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl trimethylsilanyl and benzyl groups worked efficiently with 2-halobenzo[b]furans as well, and three bioactive molecules with 2-substituted benzo[b]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[b]furans derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

scholarly journals A novel 4-aminoantipyrine-Pd(II) complex catalyzes Suzuki–Miyaura cross-coupling reactions of aryl halides

2014 ◽  
Vol 10 ◽  
pp. 2821-2826 ◽  
Author(s):  
Claudia Araceli Contreras-Celedón ◽  
Darío Mendoza-Rayo ◽  
José A Rincón-Medina ◽  
Luis Chacón-García
Keyword(s):  
Functional Groups ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Highly Active ◽  
Cross Coupling Reaction ◽  
Phenylboronic Acids

A simple and efficient catalytic system based on a Pd complex of 4-aminoantipyrine, 4-AAP–Pd(II), was found to be highly active for Suzuki–Miyaura cross-coupling of aryl iodides and bromides with phenylboronic acids under mild reaction conditions. Good to excellent product yields from the cross-coupling reaction can be achieved when the reaction is carried out in ethanol, in the open air, using low loading of 4-AAP–Pd(II) as a precatalyst, and in the presence of aqueous K2CO3 as the base. A variety of functional groups are tolerated.

scholarly journals Pd-Fe3O4/RGO: a Highly Active and Magnetically Recyclable Catalyst for Suzuki Cross Coupling Reaction using a Microfluidic Flow Reactor

2019 ◽  
Vol 14 (3) ◽  
pp. 478
Author(s):  
Hany A. Elazab ◽  
Ali R. Siamaki ◽  
B. Frank Gupton ◽  
M. Samy El-Shall
Keyword(s):  
Flow Reactor ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Highly Active ◽  
Cross Coupling Reaction ◽  
Continuous Reaction ◽  
Applied Catalysis

There are several crucial issues that need to be addressed in the field of applied catalysis. These issues are not only related to harmful environmental impact but also include process safety concerns, mass and heat transfer limitations, selectivity, high pressure, optimizing reaction conditions, scale-up issues, reproducibility, process reliability, and catalyst deactivation and recovery. Many of these issues could be solved by adopting the concept of micro-reaction technology and flow chemistry in the applied catalysis field. A microwave assisted reduction technique has been used to prepare well dispersed, highly active Pd/Fe3O4 nanoparticles supported on reduced graphene oxide nanosheets (Pd-Fe3O4/RGO), which act as a unique catalyst for Suzuki cross coupling reactions due to the uniform dispersion of palladium nanoparticles throughout the surface of the magnetite - RGO support. The Pd-Fe3O4/RGO nanoparticles have been shown to exhibit extremely high catalytic activity for Suzuki cross coupling reactions under both batch and continuous reaction conditions. This paper reported a reliable method for Suzuki cross-coupling reaction of 4-bromobenzaldehyde using magnetically recyclable Pd/Fe3O4 nanoparticles supported on RGO nanosheets in a microfluidic-based high throughput flow reactor. Organic synthesis can be performed under high pressure and temperature by using a stainless steel micro tubular flow reactor under continuous flow reaction conditions. Optimizing the reaction conditions was performed via changing several parameters including temperature, pressure, and flow rate. Generally, a scalable flow technique by optimizing the reaction parameters under high-temperature and continuous reaction conditions could be successfully developed.

A direct synthetic method for (nitronyl nitroxide)-substituted π-electronic compounds via a palladium-catalyzed cross-coupling reaction with a zinc complex

2018 ◽  
Vol 2 (3) ◽  
pp. 591-596 ◽  
Author(s):  
Shuichi Suzuki ◽  
Fumiya Nakamura ◽  
Takeshi Naota
Keyword(s):  
Zinc Complex ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Nitroxide Radical ◽  
Synthetic Method ◽  
Coupling Reactions ◽  
Nitronyl Nitroxide ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

We have developed an efficient synthetic method for (nitronyl nitroxide)-substituted π-electronic compounds via palladium-catalyzed cross-coupling reactions with a zinc complex of the parent nitronyl nitroxide radical anion.

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.

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