Efficient and practical synthesis of unsymmetrical disulfides via base-catalyzed aerobic oxidative dehydrogenative coupling of thiols

2019 ◽  
Vol 6 (13) ◽  
pp. 2220-2225 ◽  
Author(s):  
Xu Qiu ◽  
Xiaoxue Yang ◽  
Yiqun Zhang ◽  
Song Song ◽  
Ning Jiao
Keyword(s):  
Atom Economy ◽  
Reaction Conditions ◽  
Green Catalyst ◽  
Dehydrogenative Coupling ◽  
Practical Synthesis

A novel M2CO3-catalyzed aerobic oxidative heterocoupling of thiols with air as the oxidant was described for the synthesis of unsymmetrical disulfides. High atom economy, green catalyst and oxidant, mild reaction conditions, and broad substrate scope make this strategy extremely attractive.

Current Progress in the Multicomponent Catalytic Synthesis of Amidoalkyl- Naphthols: An Update

2020 ◽  
Vol 24 (5) ◽  
pp. 487-515
Author(s):  
Rajesh K. Singh ◽  
Ashima Dhiman ◽  
Shallu Chaudhary ◽  
Deo Nandan Prasad ◽  
Sahil Kumar
Keyword(s):  
Green Synthesis ◽  
Mechanism Of Action ◽  
Scientific Literature ◽  
Catalytic Synthesis ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Green Catalyst ◽  
Synthetic Intermediates ◽  
Reaction Profile

Amidoalkyl-2-naphthol is one of the vital synthetic intermediates which occupy an imperative position in medicinal chemistry due to its amazing biological, pharmacological as well as industrial and synthetic applications. Owing to its diverse pharmaceutical activities, hundreds of scientific literature are available, signifying the efficient synthesis of this intermediate using various catalysts. Most of these literature methods suffer from low yield and harsh reaction conditions that further ignited the researcher to explore for another green catalyst and fresh methodologies. This review summarizes the last five years progress in the catalytic synthesis of 1-amidoalkyl-2-naphthols using various heterogenous, homogenous and nanocatalysts along with their mechanism of action. Various advantages like green synthesis, atom economy, clean reaction profile and catalyst recovery are discussed which facilitate the scientist to probe and stimulate the study on this scaffold. In the end, the catalysts and reactions condition are organized into the tables for swift at a glance understanding of different catalysts used with their yield and time taken for the synthesis.

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

scholarly journals Nitrosonium ion catalysis: aerobic, metal-free cross-dehydrogenative carbon–heteroatom bond formation

2018 ◽  
Vol 54 (92) ◽  
pp. 13022-13025 ◽  
Author(s):  
Luis Bering ◽  
Laura D’Ottavio ◽  
Giedre Sirvinskaite ◽  
Andrey P. Antonchick
Keyword(s):  
Bond Formation ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Metal Free ◽  
Dehydrogenative Coupling ◽  
Nitrosonium Ion

Catalytic cross-dehydrogenative coupling of heteroarenes with thiophenols and phenothiazines has been developed under mild and environmentally benign reaction conditions.

scholarly journals Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

2019 ◽  
Vol 15 ◽  
pp. 874-880
Author(s):  
Razieh Navari ◽  
Saeed Balalaie ◽  
Saber Mehrparvar ◽  
Fatemeh Darvish ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Room Temperature ◽  
High Selectivity ◽  
Domino Reaction ◽  
Primary Amines ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Three Component Reaction ◽  
High Yields

An efficient approach for the synthesis of pyrazolopyridines containing the aminochromane motif through a base-catalyzed cyclization reaction is reported. The synthesis was carried out through a three-component reaction of (arylhydrazono)methyl-4H-chromen-4-one, malononitrile, primary amines in the presence of Et3N at room temperature. However, carrying out the reaction under the same conditions without base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach.

scholarly journals Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2853-2866 ◽  
Author(s):  
Arkaitz Correa ◽  
Marcos Segundo
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Bond Formation ◽  
Short Review ◽  
Great Promise ◽  
Coupling Reactions ◽  
Atom Economy ◽  
Bond Forming ◽  
Dehydrogenative Coupling ◽  
Peptide Derivatives

The functionalization of typically unreactive C(sp3)–H bonds holds great promise for reducing the reliance on existing functional groups while improving atom-economy and energy efficiency. As a result, this topic is a matter of genuine concern for scientists in order to achieve greener chemical processes. The site-specific modification of α-amino acid and peptides based upon C(sp3)–H functionalization still represents a great challenge of utmost synthetic importance. This short review summarizes the most recent advances in ‘Cross-Dehydrogenative Couplings’ of α-amino carbonyl compounds and peptide derivatives with a variety of nucleophilic coupling partners.1 Introduction2 C–C Bond-Forming Oxidative Couplings2.1 Reaction with Alkynes2.2 Reaction with Alkenes2.3 Reaction with (Hetero)arenes2.4 Reaction with Alkyl Reagents3 C–Heteroatom Bond-Forming Oxidative Couplings3.1 C–P Bond Formation3.2 C–N Bond Formation3.3 C–O and C–S Bond Formation4 Conclusions

scholarly journals Can Green Synthesis of Nanoparticles be Efficient all Year Long?

2019 ◽  
pp. 32-36
Author(s):  
Mayara Santana dos Santos ◽  
Otávio Augusto Leitão dos Santos ◽  
Sérgio Antunes Filho ◽  
Julia Corrêa dos Santos Santana ◽  
Felipe Motta de Souza ◽  
...  
Keyword(s):  
Energy Efficiency ◽  
Green Synthesis ◽  
Waste Prevention ◽  
Atom Economy ◽  
Green Technologies ◽  
Reaction Conditions ◽  
Synthesis Of Nanoparticles ◽  
Nanomaterial Synthesis ◽  
Low Toxicity ◽  
Synthesis Routes

In recent years, the search for inexpensive and eco-friendly synthesis routes has increased significantly. Nanotechnology and biotechnology have established themselves as a major ally in building green technologies for effective, stable, and non-toxic nanomaterial synthesis. [1-3]. Thus, the principles of green bio nanotechnology are associated with waste prevention, maximizing atom economy, and less use of precursors with less hazardous synthesis routes and the use of safe chemicals with low toxicity. Reaction conditions are also advantageous due to safe methodologies and increased energy efficiency.

scholarly journals Synthesis of polysubstituted spiropyrrolidines using 2-acetylfuran, 2-acetylthiophene, and 2-acetylpyrrole

2021 ◽  
Vol 21 (3) ◽  
pp. 254-259
Author(s):  
Svetlana V. Borisova ◽  
◽  
Vitaly V. Sorokin ◽  
Keyword(s):  
13C Nmr Spectroscopy ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Knoevenagel Reaction ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Stereo Selectivity ◽  
Decarboxylative Condensation ◽  
First Time

A series of novel spirooxindoles have been synthesized through three-component 1,3-dipolar cycloaddition of azomethine ylides generated in situ by the decarboxylative condensation of isatin and sarcosine with the dipolarophile 3-phenyl-1-(heteroaryl -2-yl)prop-2-en-1- one, synthesized by the Knoevenagel reaction using 2-acetylfuran, 2-acetylpyrrole, 2-acetylthiophene and substituted benzaldehydes. These compounds are used for the first time as dipolarophiles. This method has the advantages of mild reaction conditions, high atom economy, excellent yields, and high regio- and stereo-selectivity. The reaction was carried out by mixing equimolar amounts of enone and isatin, as well as a slight excess of sarcosine in isopropyl alcohol when heated to 60–70°C. Among the enones with various heterocyclic substituents, it is most convenient to use compounds containing a pyrrole fragment as dipolarophiles, since the products are obtained in a short amount of time in good yields. The use of enones obtained from 2-acetylthiophene leads to an increase in the reaction time, and from 2-acetylfuran - to a significant resinification of the reaction mixture. The structures of the compounds obtained were proved using a combination of 1H, 13C NMR spectroscopy data, as well as two-dimensional NMR experiments of heteronuclear correlation, HSQC and HMBC. Based on the data obtained, a mechanism for the formation of products has been proposed.

Practical Synthesis of Functionalized Chromeno[3,4-c]pyridine Derivatives via a CuCl2-Catalyzed Tandem Reaction of the Blaise Reaction Intermediates and 3-Cyanocoumarins

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 959-963
Author(s):  
Jian-Jun Li ◽  
Zhiwei Chen ◽  
Yangyang Fan ◽  
Lei Zheng ◽  
Zhaohai Yang
Keyword(s):  
Michael Addition ◽  
Functional Group ◽  
Tandem Reaction ◽  
Pyridine Derivatives ◽  
Reaction Intermediates ◽  
Reaction Conditions ◽  
Purification Technique ◽  
Aromatization Reaction ◽  
Oxidative Aromatization ◽  
Practical Synthesis

This work discloses a novel and efficient protocol for the construction of functionalized chromeno[3,4-c]pyridine derivatives from the Blaise reaction intermediates and 3-cyanocoumarins through a CuCl2-catalyzed sequential Michael addition/intramolecular cyclization/oxidative aromatization reaction. This new method shows the advantages of mild reaction conditions, easy workup, nonchromatographic purification technique, good functional group tolerance, and moderate to good yields.

Copper(I)-Catalyzed Sulfenylation of 1,3-Dicarbonyl Substrates with Disulfides under Mild Conditions

Synlett ◽  
2019 ◽  
Vol 30 (19) ◽  
pp. 2181-2184 ◽  
Author(s):  
Jingnan Zhao ◽  
Fan Yang ◽  
Zongyi Yu ◽  
Xiaofei Tang ◽  
Yufeng Wu ◽  
...  
Keyword(s):  
Functional Group ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Keto Esters ◽  
Mild Conditions ◽  
Easy Operation

A copper(I) iodine catalyzed sulfenylation of 1,3-dicarbonyl substrates in the presence of MeCN is presented. Various β-keto esters and β-keto amide substrates can react with disulfides to afford their corresponding products in good to excellent yields. The notable features of this protocol include high atom economy, easy operation, mild reaction conditions, and excellent functional group tolerance.

scholarly journals Sustainable Access to π-Conjugated Molecular Materials via Direct (Hetero)Arylation Reactions in Water and under Air

Molecules ◽  
2020 ◽  
Vol 25 (16) ◽  
pp. 3717
Author(s):  
Adiel Mauro Calascibetta ◽  
Sara Mattiello ◽  
Alessandro Sanzone ◽  
Irene Facchinetti ◽  
Mauro Sassi ◽  
...  
Keyword(s):  
Reaction Medium ◽  
Building Blocks ◽  
High Yield ◽  
Coupling Reactions ◽  
Materials Chemistry ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
High Boiling Point ◽  
Yield And Purity

Direct (hetero)arylation (DHA) is playing a key role in improving the efficiency and atom economy of C–C cross coupling reactions, so has impacts in pharmaceutical and materials chemistry. Current research focuses on further improving the generality, efficiency and selectivity of the method through careful tuning of the reaction conditions and the catalytic system. Comparatively fewer studies are dedicated to the replacement of the high-boiling-point organic solvents dominating the field and affecting the overall sustainability of the method. We show herein that the use of a 9:1 v/v emulsion of an aqueous Kolliphor 2 wt% solution while having toluene as the reaction medium enables the preparation of relevant examples of thiophene-containing π-conjugated building blocks in high yield and purity.

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