Pd‐Catalyzed Cross‐Dehydrogenative Coupling of 3‐Benzoyl Substituted Coumarins: Efficient Access to Indeno[2,1‐ c ]chromene‐6,7‐diones

2020 ◽  
Vol 9 (11) ◽  
pp. 1765-1768
Author(s):  
Ting Yang ◽  
Xingxing Ding ◽  
Xuecheng Zhan ◽  
Yiyi Weng
Keyword(s):  
Dehydrogenative Coupling ◽  
Efficient Access ◽  
Substituted Coumarins

Intramolecular cross dehydrogenative coupling of 4-substituted coumarins: rapid and efficient access to coumestans and indole[3,2-c]coumarins

2016 ◽  
Vol 3 (9) ◽  
pp. 1111-1115 ◽  
Author(s):  
Chao Cheng ◽  
Wen-Wen Chen ◽  
Bin Xu ◽  
Ming-Hua Xu
Keyword(s):  
Highly Efficient ◽  
Dehydrogenative Coupling ◽  
Efficient Access ◽  
Palladium Catalyzed ◽  
Substituted Coumarins

A palladium-catalyzed highly efficient and atom-economical intramolecular cross dehydrogenative coupling (CDC) reaction to access fused polyheterocycles containing a coumarin nucleus has been developed.

An Oxidant- and Catalyst-Free Electrooxidative Cross-Coupling Approach to 3-Tetrahydroisoquinoline Substituted Coumarins

2021 ◽  
Author(s):  
Yanyan Kong ◽  
Jung Keun Kim ◽  
Yabo Li ◽  
Jianye Zhang ◽  
Mengmeng Huang ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Fast Method ◽  
Catalyst Free ◽  
Dehydrogenative Coupling ◽  
Coupling Approach ◽  
Substituted Coumarins

A direct electrooxidative cross-dehydrogenative-coupling (CDC) reaction between N-aryl-tetrahydroisoquinolines and 4-hydroxycoumarins has been developed. This protocol provides a green, mild and fast method to construct 3-tetrahydroisoquinoline substituted coumarins in the absence...

DDQ-Mediated Cross-Dehydrogenative-Coupling Reaction of Secondary Amines with Dialkyl Phosphonates

Synlett ◽  
2018 ◽  
Vol 30 (01) ◽  
pp. 114-118 ◽  
Author(s):  
Ming-Xing Cheng ◽  
Jing-Wei Lei ◽  
Cai-Xia Xie
Keyword(s):  
Coupling Reaction ◽  
Transition Metal Catalysis ◽  
Secondary Amines ◽  
Metal Catalysis ◽  
New Approach ◽  
Mild Conditions ◽  
Dehydrogenative Coupling ◽  
Efficient Access ◽  
Reaction Proceeds ◽  
Dialkyl Phosphonates

This work reports a DDQ-mediated cross-dehydrogenative-coupling reaction of secondary amines with dialkyl phosphonates under mild conditions. This reaction proceeds efficiently without involving visible light or transition-metal catalysis. This new approach provides efficient access to biologically important α-aminophosphonates.

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>

Sequential C-Selective Difluoromethylation/Pd-Catalyzed Decarboxylative Protonation: An Efficient Access to Tertiary Difluoromethylated Scaffolds

2019 ◽  
Author(s):  
Nicolas Duchemin ◽  
Roberto Buccafusca ◽  
Marc Daumas ◽  
Vincent Ferey ◽  
Stellios Arseniyadis
Keyword(s):  
Drug Development ◽  
Late Stage ◽  
Efficient Access ◽  
Palladium Catalyzed ◽  
General Method

We report here a general method that allows a highly straightforward access to tertiary difluoromethylated compounds. The strategy relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and an unprecedented palladium-catalyzed decarboxylative protonation. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.<br>

Electrochemical Oxidative Esterification of Thiophenols: Efficient Access to Sulfinic Esters

2020 ◽  
Vol 17 (7) ◽  
pp. 540-547
Author(s):  
Chun-Hui Yang ◽  
Cheng Wu ◽  
Jun-Ming Zhang ◽  
Xiang-Zhang Tao ◽  
Jun Xu ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Efficient Method ◽  
High Efficiency ◽  
Building Blocks ◽  
Constant Current ◽  
Good Efficiency ◽  
Oxidative Esterification ◽  
Efficient Access ◽  
New Applications ◽  
Sulfinic Esters

Background: The sulfinic esters are important and useful building blocks in organic synthesis. Objective: The aim of this study was to develop a simple and efficient method for the synthesis of sulfinic esters. Materials and Methods: Constant current electrolysis from thiols and alcohols was selected as the method for the synthesis of sulfinic esters. Results and Discussion: A novel electrochemical method for the synthesis of sulfinic esters from thiophenols and alcohols has been developed. Up to 27 examples of sulfinic esters have been synthesized using the current methods. This protocol shows good functional group tolerance as well as high efficiency. In addition, this protocol can be easily scaled up with good efficiency. Notably, heterocycle-containing substrates, including pyridine, thiophene, and benzothiazole, gave the desired products in good yields. A plausible reaction mechanism is proposed. Conclusion: This research not only provides a green and efficient method for the synthesis of sulfinic esters but also shows new applications of electrochemistry in organic synthesis. It is considered that this green and efficient synthetic protocol used to prepare sulfinic esters will have good applications in the future.

Synthesis, In-vitro and Docking Analysis of C-3 substituted Coumarin Analogues as Anticancer Agents C-3 Substituted Coumarins as Anticancer Agents

2020 ◽  
Vol 16 ◽  
Author(s):  
Anuradha Thakur ◽  
Kamalpreet Kaur ◽  
Praveen Sharma ◽  
Ramit Singla ◽  
Sandeep Singh ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Molecular Docking ◽  
Cancer Cell ◽  
Breast Cancer Cell ◽  
Anticancer Agents ◽  
Proliferative Activity ◽  
Binding Interaction ◽  
Diverse Range ◽  
Mcf 7 ◽  
Substituted Coumarins

Background: Breast cancer (BC) is a leading cause of cancer-related deaths in women next to skin cancer. Estrogen receptors (ERs) play an important role in the progression of BC. Current anticancer agents have several drawbacks such as serious side effects and the emergence of resistance to chemotherapeutic drugs. As coumarins possess minimum side effect along with multi-drug reversal activity, it has a tremendous ability to regulate a diverse range of cellular pathways that can be explored for selective anticancer activity. Objectives: Synthesis and evaluation of new coumarin analogues for anti-proliferative activity on human breast cancer cell line MCF-7 along with exploration of binding interaction of the compounds for ER-α target protein by molecular docking. Method: In this study, the anti-proliferative activity of C-3 substituted coumarins analogues (1-17) has been evaluated against estrogen receptor-positive MCF-7 breast cancer cell lines. Molecular interactions and ADME study of the compounds were analyzed by using Schrodinger software. Results: Among the synthesized analogues 12 and 13 show good antiproliferative activity with IC50 values 1and 1.3 µM respectively. Molecular docking suggests a remarkable binding pose of all the seventeen compounds. Compounds 12 and 13 were found to exhibit dock score of -4.10 kcal/mol and -4.38 kcal/mol respectively. Conclusion: Compounds 12 and 13 showed the highest activity followed by 1 and 5. ADME properties of all compounds were in the acceptable range. The active compounds can be taken for lead optimization and mechanistic interventions for their in vivo study in the future.

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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