scholarly journals Synthetic Approach toward α-Aminomethyl-γ-butyrolactones from β-Lactam Synthons Elaborated by SmI2-mediated Reductive Coupling Reactions

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800
Author(s):  
Masaki Takahashi ◽  
Takahiro Sudo ◽  
Yusuke Murata ◽  
Tetsuya Sengoku ◽  
Hidemi Yoda
Keyword(s):  
Ring Opening ◽  
Coupling Reaction ◽  
Synthetic Approach ◽  
Coupling Reactions ◽  
Reductive Coupling ◽  
Important Class

A simple and straightforward synthetic approach was developed to access a biologically important class of α-aminomethyl-γ-butyrolactones via a β-lactam synthon strategy involving successive ring-opening and lactonization processes from α-hydroxyethyl-substituted β-lactams that were elaborated by SmI2-mediated reductive coupling reaction.

Carbocatalytic reductive coupling reactions via electron transfer from graphene to aryldiazonium salt

2017 ◽  
Vol 53 (53) ◽  
pp. 7226-7229 ◽  
Author(s):  
Naoki Morimoto ◽  
Kumika Morioku ◽  
Hideyuki Suzuki ◽  
Yumi Nakai ◽  
Yuta Nishina
Keyword(s):  
Electron Transfer ◽  
Graphene Oxide ◽  
Reduced Graphene Oxide ◽  
Coupling Reaction ◽  
Coupling Reactions ◽  
Reductive Coupling ◽  
Two Dimensional ◽  
Aryldiazonium Salt ◽  
Reduced Graphene

A reductive coupling reaction using two-dimensional nanocarbon, i.e., reduced graphene oxide (rGO), as a carbocatalyst and/or a reaction initiator was developed.

scholarly journals Carbon–Heteroatom Bond Formation via Coupling Reactions Performed on a Magnetic Nanoparticle Bed

AppliedChem ◽  
2021 ◽  
Vol 1 (2) ◽  
pp. 75-88
Author(s):  
Mahmood Tajbakhsh ◽  
Ali Ramezani ◽  
Mohammad Qandalee ◽  
Mobina Falahati ◽  
Carlos J. Durán-Valle ◽  
...  
Keyword(s):  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Significant Loss ◽  
Nucleophilic Aromatic Substitution ◽  
Solid Base ◽  
Synthetic Approach ◽  
Coupling Reactions ◽  
Aromatic Substitution ◽  
Heterogeneous Catalytic

Cross-coupling reactions leading to carbon–heteroatom bonds yield compounds that attract substantial interest due to their role as structural units in many synthetic protocols for bioactive and natural products. Therefore, many research works aim at the improvement of heterogeneous catalytic protocols. We have studied the use of magnetite nanoparticles and solid base compounds in organic synthetic reactions in carbon–heteroatom bond formation because they can be flocculated and dispersed, and reversibly controlled by applying a magnetic field. In this work, we have developed an efficient and simple synthetic approach for the C–O/C–N cross-coupling reaction under ligand-free conditions by using CuI as a catalyst and KF/Fe3O4 as a base. We performed the nucleophilic aromatic substitution of electron-deficient aryl halides and phenols. It was found that both the solvent nature and the base have a profound influence on the reaction process. This approach affords good to excellent yields of arylated products. KF/Fe3O4 displayed convenient magnetic properties and could be easily separated from the reaction using a magnet and recycled several times without significant loss of catalytic activity. This method has been successfully investigated for the Ullmann coupling reaction.

Novel cyclization and reductive coupling of bicyclic olefins with alkyl propiolates catalyzed by nickel complexes

2002 ◽  
Vol 74 (1) ◽  
pp. 69-75 ◽  
Author(s):  
Dinesh Kumar Rayabarapu ◽  
Chien-Hong Cheng
Keyword(s):  
Nickel Complex ◽  
Room Temperature ◽  
Nickel Complexes ◽  
Coupling Reaction ◽  
Coupling Reactions ◽  
Reductive Coupling ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
High Yields ◽  
Alkyl Propiolates

In this article, new metal-mediated cyclization and reductive coupling reactions of bicyclic olefins with alkynes are described. Oxabicyclic alkenes undergo cyclization with alkyl propiolates at 80 C catalyzed by nickel complexes to give benzocoumarin derivatives in high yields. The reaction of bicyclic alkenes (oxa- and azacyclic alkenes) with alkyl propiolates at room temperature in the presence of the same nickel complex gave 1,2-dihydro-napthelene derivatives in good-to-excellent yields. This reductive coupling reaction proceeds under very mild conditions in complete regio- and stereoselective fashion. A mechanism to account for the coumarin formation and the reductive coupling is proposed.

meta- and para-Functionalized Thermally Crosslinkable OLED-Materials through Selective Transition-Metal-Catalyzed Cross-Coupling Reactions

Synthesis ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 4489-4499
Author(s):  
Michael Reggelin ◽  
Matthias Hempe ◽  
Lutz Schnellbächer ◽  
Tobias Wiesner
Keyword(s):  
Transition Metal ◽  
Thermal Sensitivity ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Synthetic Approach ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Dsc Measurements ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Herein, a synthetic approach using selective transition-metal-catalyzed cross-coupling reactions to thermally crosslinkable OLED materials­ based on vinyl-functionalized arylamines is reported. In a modular approach, 9,9-dialkyl-2,7-diiodo-9H-fluorene underwent a selective Ullmann cross-coupling reaction with bromo-substituted-diphenylamines to give 9,9-dialkyl-2,7-bis(bromo-substituted-diphenylamino)-9H-fluorenes that underwent end-functionalization by the Suzuki–Miyaura reaction using potassium vinyltrifluoroborate to give the corresponding 9,9-dialkyl-2,7-bis(vinyl-substituted-diphenylamino)-9H-fluorenes. Novel meta-functionalized materials were synthesized, which are difficult to prepare by traditional synthetic pathways. The thermal behavior of the compounds was investigated by DSC measurements, indicating a lower thermal sensitivity of the meta-substituted materials than their para-functionalized analogues.

scholarly journals Umpolung synthesis of branched α-functionalized amines from imines via photocatalytic three-component reductive coupling reactions

2016 ◽  
Vol 52 (100) ◽  
pp. 14434-14437 ◽  
Author(s):  
Angel L. Fuentes de Arriba ◽  
Felix Urbitsch ◽  
Darren J. Dixon
Keyword(s):  
Amino Acid ◽  
Aromatic Aldehyde ◽  
Aromatic Amine ◽  
Coupling Reaction ◽  
Amino Acid Derivatives ◽  
Eosin Y ◽  
Coupling Reactions ◽  
Reductive Coupling ◽  
Green Led ◽  
Direct Generation

A three component reductive coupling reaction of a (hetero)aromatic amine, a (hetero)aromatic aldehyde and an electron deficient olefin catalysed by eosin Y under green LED light irradiation, for the direct generation of γ-amino acid derivatives, is described.

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.

An Unprecedented Cyano-Induced Sodium Nitrite-Catalyzed C(sp3)-H and C(sp2)-H Coupling Reaction

2018 ◽  
Vol 15 (7) ◽  
pp. 989-994 ◽  
Author(s):  
Ling Li ◽  
Bo Su ◽  
Yuxiu Liu ◽  
Qingmin Wang
Keyword(s):  
Sodium Nitrite ◽  
Oxidative Coupling ◽  
High Resolution Mass Spectrometry ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Oxidative Coupling Reaction ◽  
Oxidative Coupling Reactions

Aim and Objective: During the investigation of sodium nitrite-catalyzed oxidative coupling reaction of aryls, an unprecedented C(sp2)-H and C(sp3)-H coupling of substituted 2-aryl acetonitrile was found. Materials and Methods: The structure of the coupled product was confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry (HRMS), and comparison of its derivatives with known compounds. The effects of methoxy group in the benzene ring on the reaction were evaluated. Results: The optimized reaction conditions are summarized as follows: CF3SO3H/substrate = 1.5 equiv., NaNO2/substrate = 0.3 equiv., CH3CN as solvent. 2-(4-Methoxyphenyl)acetonitrile and 2-(3,4,5- trimethoxyphenyl)acetonitrile could also generate C(sp2)-H and C(sp3)-H coupling. The coupling reaction occurred as a typical radial mechanism. Conclusion: An unprecedented cyano-induced, NaNO2-catalyzed oxidative C(sp3)-H and C(sp2)-H coupling was reported. The reaction proceeded under very mild conditions, using O2 in the air as terminal oxidant. The unique oxidative manner might provide more inspiration for the development of intriguing oxidative coupling reactions.

Design and synthesis of 1,8-Naphthalimide Functionalized Benzothiadiazoles

2021 ◽  
Author(s):  
Rajneesh Misra ◽  
Yogjivan Rout
Keyword(s):  
Ring Opening ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Design And Synthesis ◽  
Cross Coupling Reaction ◽  
Ring Opening Reaction

A series of multi acceptor based push-pull derivatives BTD2–BTD5 were designed and synthesized via Pd-catalyzed Sonogashira cross-coupling reaction followed by [2+2] cycloaddition–electrocyclic ring-opening reaction in which benzothiadiazole (BTD, A1), naphthalimide...

Catch It If You Can: Copper-Catalyzed (Transfer) Hydrogenation Reactions and Coupling Reactions by Intercepting Reactive Intermediates Thereof

Synthesis ◽  
2020 ◽  
Vol 52 (17) ◽  
pp. 2483-2496
Author(s):  
Johannes F. Teichert ◽  
Lea T. Brechmann
Keyword(s):  
Coupling Reaction ◽  
Reactive Intermediates ◽  
Transfer Hydrogenation ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Starting Point ◽  
Bond Forming Reactions ◽  
Hydrogenation Reactions ◽  
Multicomponent Coupling Reactions ◽  
Trapping Reactions

The key reactive intermediate of copper(I)-catalyzed alkyne semihydrogenations is a vinylcopper(I) complex. This intermediate can be exploited as a starting point for a variety of trapping reactions. In this manner, an alkyne semihydrogenation can be turned into a dihydrogen­-mediated coupling reaction. Therefore, the development of copper-catalyzed (transfer) hydrogenation reactions is closely intertwined with the corresponding reductive trapping reactions. This short review highlights and conceptualizes the results in this area so far, with H2-mediated carbon–carbon and carbon–heteroatom bond-forming reactions emerging under both a transfer hydrogenation setting as well as with the direct use of H2. In all cases, highly selective catalysts are required that give rise to atom-economic multicomponent coupling reactions with rapidly rising molecular complexity. The coupling reactions are put into perspective by presenting the corresponding (transfer) hydrogenation processes first.1 Introduction: H2-Mediated C–C Bond-Forming Reactions2 Accessing Copper(I) Hydride Complexes as Key Reagents for Coupling Reactions; Requirements for Successful Trapping Reactions 3 Homogeneous Copper-Catalyzed Transfer Hydrogenations4 Trapping of Reactive Intermediates of Alkyne Transfer Semi­hydrogenation Reactions: First Steps Towards Hydrogenative Alkyne Functionalizations 5 Copper(I)-Catalyzed Alkyne Semihydrogenations6 Copper(I)-Catalyzed H2-Mediated Alkyne Functionalizations; Trapping of Reactive Intermediates from Catalytic Hydrogenations6.1 A Detour: Copper(I)-Catalyzed Allylic Reductions, Catalytic Generation of Hydride Nucleophiles from H2 6.2 Trapping with Allylic Electrophiles: A Copper(I)-Catalyzed Hydro­allylation Reaction of Alkynes 6.3 Trapping with Aryl Iodides7 Conclusion

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