Nucleophilic Aromatic Substitution of Unactivated Aryl Fluorides with Primary Aliphatic Amines by Organic Photoredox Catalysis

2020 ◽  
Vol 26 (65) ◽  
pp. 14823-14827 ◽  
Author(s):  
Weimin Shi ◽  
Jingjie Zhang ◽  
Fengqian Zhao ◽  
Wei Wei ◽  
Fang Liang ◽  
...  
Keyword(s):  
Aliphatic Amines ◽  
Nucleophilic Aromatic Substitution ◽  
Photoredox Catalysis ◽  
Aromatic Substitution ◽  
Primary Aliphatic Amines

scholarly journals Nucleophilic Aromatic Substitution of Unactivated Fluoroarenes Enabled by Organic Photoredox Catalysis

2020 ◽  
Vol 142 (40) ◽  
pp. 17187-17194 ◽  
Author(s):  
Vincent A. Pistritto ◽  
Megan E. Schutzbach-Horton ◽  
David A. Nicewicz
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Photoredox Catalysis ◽  
Aromatic Substitution

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

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.

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