Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with diverse carbon pronucleophiles: facile access to functionalized tetrahydroquinolines

2020 ◽  
Vol 56 (53) ◽  
pp. 7333-7336
Author(s):  
Guangzhe Li ◽  
Chengdong Wang ◽  
Yueqing Li ◽  
Kun Shao ◽  
Guo Yu ◽  
...  
Keyword(s):  
Synthetic Method ◽  
Dehydrogenative Coupling

Redox cross-dehydrogenative coupling of N-propargylanilines with diverse carbon pronucleophiles offers a general and efficient synthetic method to construct functionalized tetrahydroquinolines.

A Highly Efficient Copper(II)-Catalyzed Cross-Dehydrogenative-Coupling Reaction of N-Arylglycine Esters with 2-Arylimidazo[1,2-a]pyridines

Synthesis ◽  
2018 ◽  
Vol 50 (14) ◽  
pp. 2775-2783 ◽  
Author(s):  
Zhi-Qiang Zhu ◽  
Zhang-Gao Le ◽  
Li-Jin Xiao ◽  
Ying Chen ◽  
Zong-Bo Xie ◽  
...  
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Coupling Reaction ◽  
Amino Acid Esters ◽  
Synthetic Method ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Dehydrogenative Coupling ◽  
High Yields ◽  
Acid Esters

A rapid and highly efficient copper(II)-catalyzed cross-dehydrogenative coupling (CDC) reaction of N-arylglycine esters with imidazo[1,2-a]pyridines has been described. A broad range of N-arylglycine esters underwent the CDC reaction smoothly with 2-arylimidazo[1,2-a]pyridines to give α-substituted α-amino acid esters in excellent yields. This synthetic method has the advantages of high yields, good functional groups compatibility, simple operation, and mild reaction conditions. A possible mechanism for the CDC reaction is also proposed. The use of a copper salt as the catalyst and air as the terminal oxidant makes this transformation sustainable and practical.

Iron-catalyzed oxidative bis-arylation of indolin-2-ones for direct construction of quaternary carbons

2021 ◽  
Author(s):  
Ke-Xin Wu ◽  
Yi-Ze Xu ◽  
Liang Cheng ◽  
Run-Shi Wu ◽  
Peng-Ze Liu ◽  
...  
Keyword(s):  
Synthetic Method ◽  
Iron Salt ◽  
Direct Construction ◽  
Quaternary Centers ◽  
Mild Conditions ◽  
Dehydrogenative Coupling ◽  
The Cross ◽  
Quaternary Carbons

The cross-dehydrogenative coupling protocol is catalyzed by a simple iron salt, and air is used as the terminal oxidant under very mild conditions, offering a novel synthetic method for the direct construction of all-carbon quaternary centers.

Direct Cyclization of Alkenyl Thioester via Transition Metal‐hydrogen Atom Transfer/radical‐polar Crossover Mechanism

2019 ◽  
Author(s):  
Shiori Date ◽  
Kensei Hamasaki ◽  
Karen Sunagawa ◽  
Hiroki Koyama ◽  
Chikayoshi Sebe ◽  
...  
Keyword(s):  
Natural Products ◽  
Hydrogen Atom ◽  
Transition Metal ◽  
Hydrogen Atom Transfer ◽  
Synthetic Method ◽  
Atom Transfer ◽  
Reaction Conditions ◽  
Hydride Hydrogen ◽  
Sulfur Heterocycles ◽  
One Step

<div>We report here a catalytic, Markovnikov selective, and scalable synthetic method for the synthesis of saturated sulfur heterocycles, which are found in the structures of pharmaceuticals and natural products, in one step from an alkenyl thioester. Unlike a potentially labile alkenyl thiol, an alkenyl thioester is stable and easy to prepare. The powerful Co catalysis via a cobalt hydride hydrogen atom transfer and radical-polar crossover mechanism enabled simultaneous cyclization and deprotection. The substrate scope was expanded by the extensive optimization of the reaction conditions and tuning of the thioester unit.</div>

Thermally-Induced Dehydrogenative Coupling of Organosilanes and H-Terminated Silicon Quantum Dots onto Germanane Surfaces

2020 ◽  
Author(s):  
Haoyang Yu ◽  
Alyxandra Thiessen ◽  
Md Asjad Hossain ◽  
Marc Julian Kloberg ◽  
Bernhard Rieger ◽  
...  
Keyword(s):  
2D Materials ◽  
Future Generation ◽  
Optical Devices ◽  
Surface Reactivity ◽  
Organic Monolayers ◽  
Present Contribution ◽  
Thermally Induced ◽  
Dehydrogenative Coupling ◽  
Silicon Quantum Dot ◽  
Covalently Bonded

<div><div><div><p>Covalently bonded organic monolayers play important roles in defining the solution processability, ambient stability, and electronic properties of two-dimensional (2D) materials such as Ge nanosheets (GeNSs); they also hold promise of providing avenues for the fabrication of future generation electronic and optical devices. Functionalization of GeNS normally involves surface moieties linked through covalent Ge−C bonds. In the present contribution we extend the scope of surface linkages to include Si−Ge bonding and present the first demonstration of heteronuclear dehydrocoupling of organosilanes to hydride-terminated GeNSs obtained from the deintercalation and exfoliation of CaGe2. We further exploit this new surface reactivity and demonstrated the preparation of directly bonded silicon quantum dot-Ge nanosheet hybrids.</p></div></div></div>

Efficient CDI/CH3SO3H -Catalyzed, Microwave-Assisted Synthesis of 2-Substituted Benzothiazoles

2018 ◽  
Vol 16 (1) ◽  
pp. 34-39
Author(s):  
Yao-Wei Li ◽  
Pei-Ming Zhang ◽  
Rui Li ◽  
Yan Bai ◽  
Yu Yu ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Carboxylic Acids ◽  
1H Nmr ◽  
Good Yield ◽  
Microwave Assisted Synthesis ◽  
Synthetic Method ◽  
Benzothiazole Derivatives ◽  
Microwave Assisted ◽  
Highly Effective

CDI combined with CH3SO3H was found to be highly effective for the cyclization of 2-aminothiophenol derivatives with carboxylic acids under MW condition. Fourteen benzothiazole derivatives were synthesized in good yield and their structures were characterized by 1H-NMR, 13CNMR, IR and mass spectrometry. This simple, rapid synthetic method is believed to provide a useful process for the synthesis of 2-substituted benzothiazole compounds.

4-Hydroxy Pyridinium Triflate@SiO2 Nanoparticles as a Novel Efficient Catalyst for Fries Rearrangement of Aryl Esters with High Selectivity

2020 ◽  
Vol 17 (8) ◽  
pp. 654-660
Author(s):  
Shermineh Sadat Ghalehbandi ◽  
Dadkhoda Ghazanfari ◽  
Sayed Ali Ahmadi ◽  
Enayatollah Sheikhhosseini
Keyword(s):  
High Selectivity ◽  
Sio2 Nanoparticles ◽  
High Yield ◽  
Synthetic Method ◽  
Functionalized Silica ◽  
Efficient Catalyst ◽  
Fries Rearrangement ◽  
Free Condition ◽  
Solvent Free Condition ◽  
Work Up

Introduction: We developed a simple, fast and new method for the Fries rearrangement of aryl esters. Materials and Methods: 4-Hydroxy pyridinium triflate functionalized silica is a very efficient, reusable and economically available catalyst for the Fries rearrangement in solvent-free condition and under microwave irradiation. Results and Discussion: Also, a notable selectivity was observed in the presence of 4-hydroxy pyridinium triflate functionalized silica. Conclusion: Selectivity, shorter reaction time, high yield, and easy work-up are advantages of this synthetic method.

Transition-Metal-Free Synthetic Strategies for the Cross-Coupling Reactions in Water: A Green Approach

2020 ◽  
Vol 07 ◽  
Author(s):  
Tanmay Chatterjee ◽  
Nilanjana Mukherjee
Keyword(s):  
Transition Metal ◽  
Organic Solvents ◽  
Aqueous Media ◽  
Cross Coupling ◽  
Transition Metal Catalysts ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Green Approach ◽  
Dehydrogenative Coupling

Abstract: A natural driving force is always working behind the synthetic organic chemists towards the development of ‘green’ synthetic methodologies for the synthesis of useful classes of organic molecules having potential applications. The majority of the essential classes of organic transformations, including C-C and C-X (X = heteroatom) bond-forming crosscoupling reactions, cross dehydrogenative-coupling (CDC) mostly rely on the requirement of transition-metal catalysts and hazardous organic solvents. Hence, the scope in developing green synthetic strategies by avoiding the use of transitionmetal catalysts and hazardous organic solvents for those important and useful classes of organic transformations is very high. Hence, several attempts are made so far. Water being the most abundant, cheap, and green solvent in the world; numerous synthetic methods have been developed in an aqueous medium. In this review, the development of transitionmetal- free green synthetic strategies for various important classes of organic transformations such as C-C and C-X bondforming cross-coupling, cross dehydrogenative-coupling, and oxidative-coupling in an aqueous media is discussed.

Ruthenium-catalyzed synthesis of N-substituted lactams by acceptorless dehydrogenative coupling of diols with primary amines

2019 ◽  
Vol 55 (82) ◽  
pp. 12384-12387 ◽  
Author(s):  
Yanling Zheng ◽  
Xufeng Nie ◽  
Yang Long ◽  
Li Ji ◽  
Haiyan Fu ◽  
...  
Keyword(s):  
Phosphine Ligand ◽  
Primary Amines ◽  
Dehydrogenative Coupling ◽  
One Step

The first synthesis of N-substituted lactams via an acceptorless dehydrogenative coupling of diols with primary amines in one step was enabled by combining Ru3(CO)12 with a hybrid N-heterocyclic carbene–phosphine–phosphine ligand as the catalyst.

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