scholarly journals Micellar Suzuki Cross-Coupling between Thiophene and Aniline in Water and under Air

Organics ◽  
2021 ◽  
Vol 2 (4) ◽  
pp. 415-423
Author(s):  
Dawod Yousif ◽  
Silvia Tombolato ◽  
Elmehdi Ould Maina ◽  
Riccardo Po ◽  
Paolo Biagini ◽  
...  
Keyword(s):  
Room Temperature ◽  
Reaction Times ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Inert Atmosphere ◽  
Chemical Transformations ◽  
Cross Coupling Reaction ◽  
Aqueous Environments ◽  
Metal Catalyzed ◽  
High Yields

The Suzuki–Miyaura cross-coupling reaction plays a fundamental role in modern synthetic organic chemistry, both in academia and industry. For this reason, scientists continue to search for new, more effective, cheaper and environmentally friendly procedures. Recently, micellar synthetic chemistry has been demonstrated to be an excellent strategy for achieving chemical transformations in a more efficient way, thanks to the creation of nanoreactors in aqueous environments using selected surfactants. In particular, the cheap and commercially available surfactant Kolliphor EL (a polyethoxylated castor oil derivative) has been used with success to achieve metal-catalyzed transformations in water with high yields and short reaction times, with the advantage of using air-sensitive catalysts without the need for inert atmosphere. In this work, the Kolliphor EL methodology was applied to the Suzuki cross-coupling reaction between thiophene and aniline, using the highly effective catalyst Pd(dtbpf)Cl2. The cross-coupling products were achieved at up to 98% yield, with reaction times of up to only 15 min, working at room temperature and without the need for inert atmosphere.

An Iodide-Mediated Transition-Metal-Free Strategy towards Unsymmetrical Diaryl Sulfides via Arylhydrazines and Thiols

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 727-734 ◽  
Author(s):  
Farnaz Jafarpour ◽  
Mohammad Asadpour ◽  
Meysam Azizzade ◽  
Mehran Ghasemi ◽  
Saideh Rajai-Daryasarei
Keyword(s):  
Transition Metal ◽  
Room Temperature ◽  
Bond Formation ◽  
Antidepressant Drug ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Potential Utility ◽  
Metal Free ◽  
Cross Coupling Reaction ◽  
High Yields

A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C–S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.

Ferromagnetic Chain Based on Verdazyl-Nitroxide Diradical

2020 ◽  
Author(s):  
Evgeny Tretyakov ◽  
Svetlana Zhivetyeva ◽  
Pavel Petunin ◽  
Dmitry Gorbunov ◽  
Nina Gritsan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Ferromagnetic Coupling ◽  
Nitronyl Nitroxide ◽  
Triplet Ground State ◽  
One Dimensional ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Ferromagnetic Chain ◽  
High Yields

<p>Verdazyl-nitroxide diradicals were synthesized using the palladium-catalyzed cross-coupling reaction of the corresponding iodoverdazyls with a nitronyl nitroxide-2-ide gold(I) complex with high yields (up to 82%). The synthesized diradicals were found to be highly thermally stable and have a singlet (D<i>E</i><sub>ST</sub> » -64 cm<sup>–1</sup>) or triplet ground state (D<i>E</i><sub>ST</sub> ³ 25 and 100 cm<sup>–1</sup>), depending on which canonical hydrocarbon diradical type they belong to. Upon crystallization, triplet diradicals form unique one-dimensional (1D) spin <i>S</i> = 1 chains of organic diradicals with intrachain ferromagnetic coupling of <i>J</i>′/<i>k</i><sub>B</sub> from 3 to 6 K.</p>

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.

Room-Temperature, Water-Promoted, Radical-Coupling Reactions of Phenols with tert-Butyl Nitrite

Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2153-2156 ◽  
Author(s):  
Wen-Ting Wei ◽  
Hongze Liang ◽  
Wen-Ming Zhu ◽  
Weida Liang ◽  
Yi Wu ◽  
...  
Keyword(s):  
Room Temperature ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivative ◽  
Tert Butyl ◽  
Radical Coupling ◽  
Air Atmosphere ◽  
Cross Coupling Reaction ◽  
Temperature Water

A radical–radical cross-coupling reaction of phenols with tert-butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C–N bonds under an air atmosphere at room temperature, providing the ortho-nitrated phenol derivative in moderate to good yields.

Pyrido[1,2-a]pyrazine - Startprodukte für regioselektive Ringtransformationen und supramolekulare Architekturen / Pyrido[1,2-a]pyrazines - Starting Materials for Regioselective Ringtransformation Reactions and Supramolecular Architectures

2002 ◽  
Vol 57 (4) ◽  
pp. 471-478 ◽  
Author(s):  
D. Müller ◽  
B. Frank ◽  
R. Beckert ◽  
H. Görls
Keyword(s):  
Cycloaddition Reaction ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Building Blocks ◽  
Ring Transformation ◽  
Supramolecular Architectures ◽  
Cross Coupling Reaction ◽  
Metal Catalyzed

The easily available pyrido[1,2-a]pyrazines of type 1 are versatile building blocks for ring transformation reactions.W ith heterocyclic quinones such as quinoline-2,5,8-triones 4a-c, a highly regioselective [4+2]-cycloaddition reaction takes place in the first step, followed by a ring transformation cascade.T he 1,6-diazaanthracene-2,9,10-triones 5a-e, which possess an additional bipyridine substructure, could be isolated as main products.In order to modify the starting products of type 1, a metal-catalyzed cross-coupling reaction with acetylenic benzoic esters 9a,b has been performed.T he modified pyridopyrazines 10a,b which were obtained in good yields could be transformed by analogy to 1a,b into ring-fused heterocyclic quinones 12a,b.

Synthesis and Application of Tetrafluoroethylene (CF2CF2)-Containing Acetylene Derivatives

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1947-1958
Author(s):  
Tsutomu Konno ◽  
Gen Egashira ◽  
Chihiro Kajimoto ◽  
Takuto Kataoka ◽  
Shigeyuki Yamada
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Alder Reaction ◽  
Diels Alder ◽  
Benzene Derivatives ◽  
Diels Alder Reaction ◽  
Cross Coupling Reaction ◽  
Oxidative Aromatization ◽  
High Yields ◽  
Acetylene Derivatives

On treating 1,3,4-tribromo-1,1,2,2-tetrafluorobutane, readily prepared from commercially available 4-bromo-3,3,4,4-tetrafluorobut-1-ene, with 3.3 equivalents of LHMDS at 0 °C in THF, the corresponding lithium acetylide could be prepared quantitatively. The acetylide reacted well with various aldehydes, ketones, or chlorosilanes to give the corresponding acetylene derivatives in high yields. It was also found that various iodoarenes could participate in the cross-coupling reaction with the zinc acetylide, readily prepared from the lithium acetylide and ZnCl2·TMEDA complex, in the presence of Pd(PPh3)4 to bring about the adducts in high yields. Thus-obtained acetylene derivatives underwent smooth Diels–Alder reaction with various 1,3-dienes to afford the corresponding 1,4- or 1,3-cyclohexadiene derivatives. In addition, it was revealed that the oxidative aromatization of the resulting cyclohexadiene derivatives with DDQ took place very smoothly, providing the multi-substituted benzene derivatives having a tetrafluoro­ethylene group.

scholarly journals A New Heterogeneous Catalyst Obtained via Supramolecular Decoration of Graphene with a Pd2+ Azamacrocyclic Complex

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2714 ◽  
Author(s):  
Matteo Savastano ◽  
Paloma Arranz-Mascarós ◽  
Maria Paz Clares ◽  
Rafael Cuesta ◽  
Maria Luz Godino-Salido ◽  
...  
Keyword(s):  
Heterogeneous Catalyst ◽  
Self Assembly ◽  
Room Temperature ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Assembly Process ◽  
Efficient Catalyst ◽  
Mild Conditions ◽  
Cross Coupling Reaction ◽  
Green Procedure

A new G-(H2L)-Pd heterogeneous catalyst has been prepared via a self-assembly process consisting in the spontaneous adsorption, in water at room temperature, of a macrocyclic H2L ligand on graphene (G) (G + H2L = G-(H2L)), followed by decoration of the macrocycle with Pd2+ ions (G-(H2L) + Pd2+ = G-(H2L)-Pd) under the same mild conditions. This supramolecular approach is a sustainable (green) procedure that preserves the special characteristics of graphene and furnishes an efficient catalyst for the Cu-free Sonogashira cross coupling reaction between iodobenzene and phenylacetylene. Indeed, G-(H2L)-Pd shows an excellent conversion (90%) of reactants into diphenylacetylene under mild conditions (50 °C, water, aerobic atmosphere, 14 h). The catalyst proved to be reusable for at least four cycles, although decreasing yields down to 50% were observed.

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.

Analysis of the water extract of waste papaya bark ash and its implications as an in situ base in the ligand-free recyclable Suzuki–Miyaura coupling reaction

RSC Advances ◽  
2016 ◽  
Vol 6 (34) ◽  
pp. 28981-28985 ◽  
Author(s):  
Manashi Sarmah ◽  
Anindita Dewan ◽  
Manoj Mondal ◽  
Ashim J. Thakur ◽  
Utpal Bora
Keyword(s):  
Room Temperature ◽  
Water Extract ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Basic Medium ◽  
Low Temperature Combustion ◽  
Cross Coupling Reaction ◽  
Ligand Free ◽  
Temperature Combustion

The conversion of waste papaya-bark to ash–water extract via low-temperature combustion, and its utilization as an efficient and eco-friendly in situ basic medium for Suzuki–Miyaura cross-coupling reaction at room temperature are reported.

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