Direct Synthesis of Vicinal Tricarbonyl Amides by Coupling of α-Oxo Acid Chlorides with Carbamoylsilanes

Synthesis ◽  
2019 ◽  
Vol 51 (15) ◽  
pp. 2977-2983
Author(s):  
Yuling Han ◽  
Yuping Li ◽  
Shenghua Han ◽  
Pengpeng Zhang ◽  
Jianxin Chen
Keyword(s):  
Oxalyl Chloride ◽  
Direct Synthesis ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Synthetic Method ◽  
Acid Chlorides ◽  
Mild Conditions ◽  
Cross Coupling Reaction ◽  
The Cross

A convenient synthetic method for vicinal tricarbonyl amides by the cross-coupling reaction of α-oxo acid chlorides with carbamoylsilanes is developed. The reaction tolerates a broad range of substituents on the amido nitrogen of carbamoylsilanes, and directly affords good yields of vicinal tricarbonyl amides under mild conditions without use of oxidants. The reaction of carbamoylsilanes with oxalyl chloride has also been explored, and is accompanied by decarbonylation to give vicinal tricarbonyl amides.

Pd-catalyzed desulfitative arylation of olefins by N-methoxysulfonamide

2022 ◽  
Author(s):  
Subhadra Ojha ◽  
Niranjan Panda
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Type Reaction ◽  
Cross Coupling Reaction ◽  
The Cross

A novel Pd-catalyzed protocol desulfitative Heck type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtainaryl alkenes....

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.

scholarly journals A DFT Study on FeI/FeII/FeIII Mechanism of the Cross-Coupling between Haloalkane and Aryl Grignard Reagent Catalyzed by Iron-SciOPP Complexes

Molecules ◽  
2020 ◽  
Vol 25 (16) ◽  
pp. 3612 ◽  
Author(s):  
Akhilesh Sharma ◽  
Masaharu Nakamura
Keyword(s):  
Density Functional ◽  
Molecular Mechanic ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Dft Study ◽  
Reaction Pathways ◽  
Hydrogen Elimination ◽  
Cross Coupling Reaction ◽  
The Cross ◽  
A Chain

To explore plausible reaction pathways of the cross-coupling reaction between a haloalkane and an aryl metal reagent catalyzed by an iron–phosphine complex, we examine the reaction of FeBrPh(SciOPP) 1 and bromocycloheptane employing density functional theory (DFT) calculations. Besides the cross-coupling, we also examined the competitive pathways of β-hydrogen elimination to give the corresponding alkene byproduct. The DFT study on the reaction pathways explains the cross-coupling selectivity over the elimination in terms of FeI/FeII/FeIII mechanism which involves the generation of alkyl radical intermediates and their propagation in a chain reaction manner. The present study gives insight into the detailed molecular mechanic of the cross-coupling reaction and revises the FeII/FeII mechanisms previously proposed by us and others.

scholarly journals Pd(CH3CN)2Cl2/Pipecolinic Acid as a Highly Efficient Catalytic System for Suzuki-Miyaura Cross-coupling Reaction of Bromoaryl Carboxylic Acids in Water

Catalysts ◽  
2019 ◽  
Vol 9 (1) ◽  
pp. 86 ◽  
Author(s):  
Xiaogang Li ◽  
Wenbin Zhang ◽  
Leiqing Fu ◽  
Mengping Guo
Keyword(s):  
Catalytic System ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Catalytic Performance ◽  
High Turnover ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Cross Coupling Reaction ◽  
Pipecolinic Acid ◽  
Excellent Catalytic Performance

In this study, a convenient and highly efficient catalytic system for the Suzuki-Miyaura coupling reaction was investigated under mild conditions. A combination of Pd(CH3CN)2Cl2 and pipecolinic acid showed excellent catalytic performance and afforded high turnover numbers; turnover numbers were up to 4.9 × 105 for the coupling reaction of 4-bromobenzoic acid and tetraphenylboron sodium. The catalytic system was also effective for the indexes of 4-bromobenzoic acid, and high turnover numbers were obtained.

Pd/APN-Mn(BTC) as novel, highly efficient, and recyclable catalyst for Suzuki–Miyaura cross coupling reaction

2020 ◽  
Vol 98 (8) ◽  
pp. 445-452
Author(s):  
Hamid Aliyan ◽  
Razieh Fazaeli
Keyword(s):  
Palladium Nanoparticles ◽  
Metal Organic Framework ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Analytical Techniques ◽  
Mild Conditions ◽  
Cross Coupling Reaction ◽  
Highly Dispersed ◽  
Metal Organic ◽  
Adsorption Desorption

A novel, heterogeneous, and bifunctional metal organic framework containing palladium and manganese, Pd/APN-Mn(BTC), has been prepared and completely characterized using FTIR, XRD, SEM-EDS, N2 adsorption–desorption, TG-DTG, NH3-TPD, and ICP analytical techniques. The APN-Mn(BTC) framework has been shown to be a useful platform for the stabilization and support of palladium nanoparticles (Pd NPs). Very effective catalytic activity has been exhibited by the highly dispersed Pd particles, Pd-NPs/APN-Mn(BTC), in the Suzuki–Miyaura cross-coupling reaction with reasonable to excellent reaction yields under mild conditions in H2O–ethanol solvent.

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