A PEG/copper(i) halide cluster as an eco-friendly catalytic system for C–N bond formation

2018 ◽  
Vol 47 (22) ◽  
pp. 7463-7470 ◽  
Author(s):  
Cheng-An Li ◽  
Wei Ji ◽  
Jian Qu ◽  
Su Jing ◽  
Fei Gao ◽  
...  
Keyword(s):  
Catalytic System ◽  
Bond Formation ◽  
High Yield ◽  
Reaction Conditions ◽  
Halide Cluster

The PEG/ferrocenyltelluroether-based copper(i) halide cluster is an eco-friendly system in C–N formation with mild reaction conditions, high yield and easy recyclability.

Ru-catalyzed oxidation and C–C bond formation of indoles for the synthesis of 2-indolyl indolin-3-ones under mild reaction conditions

2020 ◽  
Vol 98 (11) ◽  
pp. 667-669
Author(s):  
Xiao-Yu Zhou ◽  
Xia Chen
Keyword(s):  
Catalytic Oxidation ◽  
Bond Formation ◽  
High Yield ◽  
Target Product ◽  
Reaction Conditions ◽  
Formation Reaction ◽  
Butyl Hydroperoxide ◽  
Tert Butyl Hydroperoxide ◽  
Catalyzed Oxidation ◽  
Oxidation System

Herein, we described a ruthenium catalyzed oxidation and C–C bond formation reaction of 2-alkyl or 2-aryl substituted indoles using tert-butyl hydroperoxide (TBHP) as oxidant. Coupled with cascade transformation, it provided a mild catalytic oxidation system for the synthesis of 2-indolylindolin-3-ones. The reaction could readily occur using RuCl3·3H2O as catalyst, and the target product was obtained with medium to high yield.

Environment Friendly and Recyclable CuCl2-mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base and Solvent

Synthesis ◽  
2021 ◽  
Author(s):  
Guodong Shen ◽  
Qichao Lu ◽  
Zeyou Wang ◽  
Weiwei Sun ◽  
Yalin Zhang ◽  
...  
Keyword(s):  
Catalytic System ◽  
Bond Formation ◽  
Environmentally Friendly ◽  
Industrial Applications ◽  
Reaction Conditions ◽  
Environment Friendly ◽  
Economic Strategy ◽  
Formation Reaction ◽  
Simple Reaction ◽  
Coupling Strategy

Simple reaction conditions and recyclable reagents are an irreplaceable advantage for environmentally friendly industrial applications. An environment friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2 catalyzed C-S bond formation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N’-dimethylethane-1,2-diamine (DMEDA) as ligand, base and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates is compatible to give the corresponding products in good to excellent yields. Both the reaction reagents of the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable and recyclable for more than 5 cycles.

Gold Catalyzed Hydroamination of Propargylic Alcohols: Controlling Divergent Reaction Pathways to Access 1,3-Aminoalcohols, 3-Hydroxyketones or 3-Aminoketones

2018 ◽  
Author(s):  
Victor Laserna ◽  
Tom Sheppard
Keyword(s):  
Gold Catalysis ◽  
Reaction Pathways ◽  
High Yield ◽  
Reaction Conditions ◽  
Propargylic Alcohols ◽  
Catalytic Quantity ◽  
Selective Formation ◽  
General Method

A versatile approach to the valorization of propargylic alcohols is reported, enabling controlled access to three different products from the same starting materials. Firstly, a general method for the hydroamination of propargylic alcohols with anilines is described using gold catalysis to give 3-hydroxy imines with complete regioselectivity. These 3-hydroxyimines can be reduced to give 1,3-aminoalcohols with high syn seletivity. Alternatively, by using a catalytic quantity of aniline, 3-hydroxyketones can be obtained in high yield directly from propargylic alcohols. Further manipulation of the reaction conditions enables the selective formation of 3-aminoketones via a rearrangement/hydroamination pathway.<br>

Pd Catalyzed N1/N4 Arylation of Piperazine for Synthesis of Drugs, Biological and Pharmaceutical Targets: An Overview of Buchwald Hartwig Amination Reaction of Piperazine in Drug Synthesis

2018 ◽  
Vol 15 (2) ◽  
pp. 208-220 ◽  
Author(s):  
Vaibhav Mishra ◽  
Tejpal Singh Chundawat
Keyword(s):  
Bond Formation ◽  
Catalyst Design ◽  
Biologically Active ◽  
Reaction Conditions ◽  
Biological Targets ◽  
Amination Reaction ◽  
Drug Synthesis ◽  
Substituted Piperazine ◽  
Approved Drugs ◽  
Fda Approved Drugs

Background: Substituted piperazine heterocycles are among the most significant structural components of pharmaceuticals. N1/N4 substituted piperazine containing drugs and biological targets are ranked 3rd in the top most frequent nitrogen heterocycles in U.S. FDA approved drugs. The high demand of N1/N4 substituted piperazine containing biologically active compounds and U.S. FDA approved drugs, has prompted the development of Pd catalyzed C-N bond formation reactions for their synthesis. Buchwald-Hartwig reaction is the key tool for the synthesis of these compounds. Objective: This review provides strategies for Pd catalyzed C-N bond formation at N1/N4 of piperazine in the synthesis of drugs and biological targets with diverse use of catalyst-ligand system and reaction parameters. Conclusion: It is clear from the review that a vast amount of work has been done in the synthesis of N1/N4 substituted piperazine containing targets under the Pd catalyzed Buchwald-Hartwig amination of aryl halides by using different catalyst-ligand systems. These methods have become increasingly versatile as a result of innovation in catalyst design and improvements in reaction conditions. This review gives an overview of recent utilization of Buchwald-Hartwig amination reaction in drug/target synthesis.

Addition of Tetrachloromethane to 1,5-Hexadiene

1992 ◽  
Vol 57 (2) ◽  
pp. 393-396 ◽  
Author(s):  
Martin Kotora ◽  
Milan Hájek
Keyword(s):  
Palladium Catalyst ◽  
Adduct Formation ◽  
High Yield ◽  
Reaction Conditions ◽  
Dibenzoyl Peroxide

The 2 : 1 adduct as the final product of the addition of tetrachloromethane to 1,5-hexadiene catalyzed by copper(I)-butylamine complex was obtained in high yield (96%) under mild reaction conditions. Predominant 1 : 1 adduct formation was observed in the presence of a palladium catalyst or dibenzoyl peroxide initiator.

Modern Organic Synthesis in the Laboratory

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Organic Chemistry ◽  
Graduate Students ◽  
Organic Synthesis ◽  
Functional Group ◽  
Bond Formation ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Oxidation Reduction ◽  
Carbon Carbon Bond ◽  
Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

Chemoselective Double Michael Addition: Synthesis of 2,6-Diarylspiro[Cyclohexane-1,3′-Indoline]-2′,4-Diones via Addition of Indolin-2-One to Divinyl Ketones

2017 ◽  
Vol 41 (3) ◽  
pp. 168-171 ◽  
Author(s):  
Zheng Li ◽  
Jiasheng Li ◽  
Jingya Yang
Keyword(s):  
Michael Addition ◽  
High Yield ◽  
Reaction Conditions ◽  
Michael Additions

Seventeen examples of 2,6-diarylspiro[cyclohexane-1,3′-indoline]-2′4-diones were efficiently prepared by the Cs2CO3-catalysed chemoselective double Michael additions of indolin-2-one to divinyl ketones. This method has the advantage of high chemoselectivity, mild reaction conditions, high yield and atom- and step-economy.

scholarly journals Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1615
Author(s):  
Amy Boylan ◽  
Thien S. Nguyen ◽  
Brian J. Lundy ◽  
Jian-Yuan Li ◽  
Ravikrishna Vallakati ◽  
...  
Keyword(s):  
Positive Charge ◽  
Bond Formation ◽  
Conjugate Addition ◽  
Reaction Rates ◽  
Boronic Acids ◽  
Key Factors ◽  
Resonance Contribution ◽  
Reaction Conditions ◽  
Resonance Effects ◽  
Resonance Stabilization

Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.

scholarly journals Ring-Opening Copolymerization of Cyclohexene Oxide and Cyclic Anhydrides Catalyzed by Bimetallic Scorpionate Zinc Catalysts

Polymers ◽  
2021 ◽  
Vol 13 (10) ◽  
pp. 1651
Author(s):  
Felipe de la Cruz-Martínez ◽  
Marc Martínez de Sarasa Buchaca ◽  
Almudena del Campo-Balguerías ◽  
Juan Fernández-Baeza ◽  
Luis F. Sánchez-Barba ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Reaction Mechanism ◽  
Catalytic System ◽  
Phthalic Anhydride ◽  
Ring Opening ◽  
High Selectivity ◽  
Zinc Complexes ◽  
Cyclohexene Oxide ◽  
Reaction Conditions ◽  
Cyclic Anhydrides

The catalytic activity and high selectivity reported by bimetallic heteroscorpionate acetate zinc complexes in ring-opening copolymerization (ROCOP) reactions involving CO2 as substrate encouraged us to expand their use as catalysts for ROCOP of cyclohexene oxide (CHO) and cyclic anhydrides. Among the catalysts tested for the ROCOP of CHO and phthalic anhydride at different reaction conditions, the most active catalytic system was the combination of complex 3 with bis(triphenylphosphine)iminium as cocatalyst in toluene at 80 °C. Once the optimal catalytic system was determined, the scope in terms of other cyclic anhydrides was broadened. The catalytic system was capable of copolymerizing selectively and efficiently CHO with phthalic, maleic, succinic and naphthalic anhydrides to afford the corresponding polyester materials. The polyesters obtained were characterized by spectroscopic, spectrometric, and calorimetric techniques. Finally, the reaction mechanism of the catalytic system was proposed based on stoichiometric reactions.

Cleavage of C=N derivatives and Oxidation of Thiols in Water under Neutral Conditions with 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bischloride

2007 ◽  
Vol 2007 (8) ◽  
pp. 486-489 ◽  
Author(s):  
Mahmood Tajbakhsh ◽  
Setareh Habibzadeh
Keyword(s):  
Carbonyl Compounds ◽  
High Yield ◽  
Reaction Conditions ◽  
Neutral Conditions

1,4-Diazabicyclo[2,2,2]octane (DABCO) is easily chlorinated and gives a complex which efficiently converts aliphatic and aromatic oximes, phenylhydrazones and semicarbazones to their corresponding carbonyl compounds in water at 50°C in high yield. This reagent can also be used for conversion of thiols to their compounding disulfide under the same reaction conditions. DABCO is quantitatively recovered which can be rechlorinated and reused several times.

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