From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

2018 ◽  
Vol 130 (14) ◽  
pp. 3703-3707 ◽  
Author(s):  
Dong-Yu Wang ◽  
Ze-Kun Yang ◽  
Chao Wang ◽  
Ao Zhang ◽  
Masanobu Uchiyama
Keyword(s):  
Synthetic Method ◽  
Mild Conditions ◽  
Aryl Ethers

From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

2018 ◽  
Vol 57 (14) ◽  
pp. 3641-3645 ◽  
Author(s):  
Dong-Yu Wang ◽  
Ze-Kun Yang ◽  
Chao Wang ◽  
Ao Zhang ◽  
Masanobu Uchiyama
Keyword(s):  
Synthetic Method ◽  
Mild Conditions ◽  
Aryl Ethers

scholarly journals One-Pot Synthesis of α-Substituted Acrylates

SynOpen ◽  
2018 ◽  
Vol 02 (02) ◽  
pp. 0161-0167
Author(s):  
Magdalini Matziari ◽  
Yixin Xie
Keyword(s):  
Amino Acids ◽  
Reaction Times ◽  
Synthetic Method ◽  
One Pot ◽  
Biologically Relevant ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Acrylic Esters ◽  
Natural Amino Acids ◽  
Work Up

A simple and efficient synthetic method towards α-substituted acrylic esters has been developed using the Horner–Wadsworth–Emmons (HWE) reaction with HCHO after alkylation of phosphonoacetates in a one-pot reaction. This method allows the smooth introduction of various side-chains, such as natural amino acids and other biologically relevant substituents. The use of mild conditions, inexpensive reagents, short reaction times and simple work-up and purification steps provides an effective and general alternative to cumbersome multistep and low-yielding procedures described to date.

Efficient hydrogenolysis of aryl ethers over Ce-MOF supported Pd NPs under mild conditions: mechanistic insight using density functional theoretical calculations

2020 ◽  
Vol 10 (20) ◽  
pp. 6892-6901
Author(s):  
Ashish Kumar Kar ◽  
Surinder Pal Kaur ◽  
T. J. Dhilip Kumar ◽  
Rajendra Srivastava
Keyword(s):  
Catalytic Activity ◽  
Adsorption Energy ◽  
Density Functional ◽  
Theoretical Calculations ◽  
Desorption Energy ◽  
Mild Conditions ◽  
Mechanistic Insight ◽  
Aryl Ethers ◽  
Benzyl Phenyl Ether ◽  
Supported Pd

The significant Pd0 content and optimum bonding of the reactant & product (higher adsorption energy of benzyl phenyl ether and lower desorption energy for phenol) are responsible for the exceptional catalytic activity of Pd/Ce-MOF.

Synthesis of fluorinated aryl ethers via selective C–F functionalization with polyfluorobenzenes and carbonates under mild conditions

2015 ◽  
Vol 56 (32) ◽  
pp. 4689-4693 ◽  
Author(s):  
Guanghui Yang ◽  
Zhiqun Yu ◽  
Xinpeng Jiang ◽  
Chuanming Yu
Keyword(s):  
Mild Conditions ◽  
Aryl Ethers

scholarly journals Chemoselective activation of amide carbonyls towards nucleophilic reagents

2016 ◽  
Author(s):  
Bartłomiej Furman
Keyword(s):  
Chemical Biology ◽  
Grignard Reagents ◽  
Synthetic Method ◽  
Important Class ◽  
Selective Activation ◽  
One Pot ◽  
Mild Conditions ◽  
Nucleophilic Reagents ◽  
Danishefsky's Diene

Amides represent an important class of compounds in chemistry, chemical biology and pharmaceutical industry. Their broad utility in many fields is closely tied to the structure of the amide moiety which endows these compounds with unique features. The low reactivity of amide carbonyls towards nucleophiles is a major obstacle to their further functionalization. Selective activation of amides and lactams enables access to novel reactivity pathways and opens up intriguing perspectives in synthesis. Recently, we have demonstrated that upon treatment with Cp2Zr(H)Cl (Schwartz’s reagent), five- and six-membered lactams, including sugar- and hydroxy acid-derived lactams, can be easily converted into imines under mild conditions. In addition, as was also shown, in situ generated cyclic imines can be directly subjected to further reactions with nucleophilic reagents such as allyltributylstannane, Grignard reagents, enolates or Danishefsky’s diene to afford α-functionalized pyrrolidines, piperidines and polyhydroxylated pyrrolidine peptidomimetic scaffolds in a one-pot manner. The key advantage of the presented approach is the simplicity and convenience of generation of sugar-derived imines from readily available starting materials: sugar-derived lactams. The use of sugar-derived lactams as cyclic imine precursors is crucial to the efficiency of the described synthetic method. These compounds are more readily prepared, handled, and stored than the alternative precursors of cyclic imines such as nitrones, N-chloroamines or azido aldehydes. In the second part of the lecture a method for preparing 2,3-disubstituted indoles from commercially available isatins will be briefly presented.

scholarly journals Chemoselective activation of amide carbonyls towards nucleophilic reagents

2016 ◽  
Author(s):  
Bartłomiej Furman
Keyword(s):  
Chemical Biology ◽  
Grignard Reagents ◽  
Synthetic Method ◽  
Important Class ◽  
Selective Activation ◽  
One Pot ◽  
Mild Conditions ◽  
Nucleophilic Reagents ◽  
Danishefsky's Diene

Amides represent an important class of compounds in chemistry, chemical biology and pharmaceutical industry. Their broad utility in many fields is closely tied to the structure of the amide moiety which endows these compounds with unique features. The low reactivity of amide carbonyls towards nucleophiles is a major obstacle to their further functionalization. Selective activation of amides and lactams enables access to novel reactivity pathways and opens up intriguing perspectives in synthesis. Recently, we have demonstrated that upon treatment with Cp2Zr(H)Cl (Schwartz’s reagent), five- and six-membered lactams, including sugar- and hydroxy acid-derived lactams, can be easily converted into imines under mild conditions. In addition, as was also shown, in situ generated cyclic imines can be directly subjected to further reactions with nucleophilic reagents such as allyltributylstannane, Grignard reagents, enolates or Danishefsky’s diene to afford α-functionalized pyrrolidines, piperidines and polyhydroxylated pyrrolidine peptidomimetic scaffolds in a one-pot manner. The key advantage of the presented approach is the simplicity and convenience of generation of sugar-derived imines from readily available starting materials: sugar-derived lactams. The use of sugar-derived lactams as cyclic imine precursors is crucial to the efficiency of the described synthetic method. These compounds are more readily prepared, handled, and stored than the alternative precursors of cyclic imines such as nitrones, N-chloroamines or azido aldehydes. In the second part of the lecture a method for preparing 2,3-disubstituted indoles from commercially available isatins will be briefly presented.

Selective aromatic chlorination of activated arenes with sodium chlorite, (salen)manganese(III) complex, and alumina in dichloromethane

1997 ◽  
Vol 75 (12) ◽  
pp. 1905-1912 ◽  
Author(s):  
Masao Hirano ◽  
Shigetaka Yakabe ◽  
Hiroyuki Monobe ◽  
Takashi Morimoto
Keyword(s):  
Biphasic System ◽  
Sodium Chlorite ◽  
Alkyl Aryl ◽  
Mild Conditions ◽  
Aryl Ethers ◽  
Phenyl Ethers ◽  
Alkyl Aryl Ethers

The reaction of alkyl phenyl ethers with sodium chlorite in dichloromethane in the presence of a (salen)manganese(III) complex and alumina preloaded with a small amount of water afforded monochlorination products with unusually high para selectivities under mild conditions. The NaClO2-based biphasic system can also be successfully used for the regioselective monochlorination of substituted anisoles and polymethoxybenzenes. Keywords: aromatic chlorination, alkyl aryl ethers, sodium chlorite, (salen)manganese(III) complex, alumina.

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