Catalytic Atroposelective Dynamic Kinetic Resolutions and Kinetic Resolutions towards 3-arylquinolines via SNAr

2021 ◽  
Author(s):  
Mariel Cardenas ◽  
Mirza A Saputra ◽  
Deane A Gordon ◽  
Andrea N Sanchez ◽  
Nobuyuki Yamamoto ◽  
...  
Keyword(s):  
Cinchona Alkaloid ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Kinetic Resolutions

Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolines via the nucleophilic aromatic substitution (SNAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These...

scholarly journals Machine learning meets mechanistic modelling for accurate prediction of experimental activation energies

2021 ◽  
Author(s):  
Kjell Jorner ◽  
Tore Brinck ◽  
Per-Ola Norrby ◽  
David Buttar
Keyword(s):  
Machine Learning ◽  
Activation Energies ◽  
Accurate Prediction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Mechanistic Modelling

Hybrid reactivity models, combining mechanistic calculations and machine learning with descriptors, are used to predict barriers for nucleophilic aromatic substitution.

Enantioselective Nucleophilic Aromatic Substitution Reaction of Azlactones to Synthesize Quaternary α-Amino Acid Derivatives

Synlett ◽  
2020 ◽  
Author(s):  
Xiaohua Liu ◽  
Yi Li ◽  
Hao Pan ◽  
Wang-Yuren Li ◽  
Xiaoming Feng
Keyword(s):  
Hydrogen Bonding ◽  
Charge Transfer ◽  
Amino Acid ◽  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Amino Acid Derivatives ◽  
Amino Acid Esters ◽  
Aromatic Substitution ◽  
Charge Transfer Interaction ◽  
Acid Esters

AbstractAn asymmetric organocatalytic nucleophilic aromatic substitution reaction of azlactones with electron-deficient aryls was established. A variety of α-aryl α-alkyl α-amino acid esters and peptides were obtained in decent yields and stereoselectivities. A new bifunctional catalytic mode involving charge-transfer interaction and hydrogen bonding is proposed to explain the enantioselectivity.

Nucleophilic aromatic substitution using Et3SiH/cat. t-Bu-P4 as a system for nucleophile activation

2007 ◽  
pp. 2264 ◽  
Author(s):  
Masahiro Ueno ◽  
Misato Yonemoto ◽  
Masahiro Hashimoto ◽  
Andrew E. H. Wheatley ◽  
Hiroshi Naka ◽  
...  
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Nucleophile Activation

Novel One-Pot Synthesis of Xanthones via Sequential Fluoride Ion-Promoted Fries-Type Rearrangement and Nucleophilic Aromatic Substitution

Synlett ◽  
2013 ◽  
Vol 24 (19) ◽  
pp. 2575-2580 ◽  
Author(s):  
Takashi Matsumoto ◽  
Yuuki Fujimoto ◽  
Ryohei Itakura ◽  
Hiroki Hoshi ◽  
Hikaru Yanai ◽  
...  
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Fluoride Ion ◽  
Aromatic Substitution ◽  
One Pot ◽  
One Pot Synthesis

scholarly journals The use of bisphthalonitriles in the synthesis of side-strapped 1,11,15,25-tetrasubstituted phthalocyanines

1996 ◽  
Vol 74 (3) ◽  
pp. 307-318 ◽  
Author(s):  
Clifford C. Leznoff ◽  
David M. Drew
Keyword(s):  
Key Words ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Pure Compounds

Nucleophilic aromatic substitution reactions of 3-nitrophthalonitrile yield 3-hydroxyphthalonitrile and 3-neopentoxyphthalonitrile, the latter of which condensed to 1,8,15,22-tetraneopentoxyphthalocyanine as a mixture of isomers. Bisphthalonitriles such as 1,3-bis(2′,3′-dicyanophenoxy)-2,2-dipentylpropane, 1,3-bis(2′,3′-dicyanophenoxy)-2,2-diethylpropane, 1,3-bis(2′,3′-dicyanophenoxy)-2,2-dioctylpropane, and 1,3-bis(2′,3′-dicyanophenoxy)-2-methyl-2-trityloxymethylpropane all gave bis-crown-like 1,11,15,25-tetrasubstituted phthalocyanines as pure compounds when treated with lithium octoxide in 1-octanol at 196 °C. A host of nine other bisphthalonitriles including 1,5-bis(2′,3′-dicyanophenoxy)-3-oxapentane, 1,1-bis(2′,3′-dicyanophenoxymethyl)cyclohexane, 1,2-bis(2′,3′-dicyanophenoxymethyl)benzene, and 2,5-bis(2′,3′-dicyanophenoxymethyl)furan did not dimerize to mononuclear phthalocynaines. The "gem dimethyl" effect was suggested as a reason for the successful macrocyclizations. Key words: nucleophilic aromatic substitution, phthalonitriles, bisphthalonitriles, 1,11,15,25-tetrasubstituted phthalocyanines.

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