Regiospecific nucleophilic aromatic substitution: conjugate addition of active methylene compounds to quinone monoacetals and aromatization of the adducts

1980 ◽  
Vol 45 (7) ◽  
pp. 1218-1224 ◽  
Author(s):  
Kathlyn A. Parker ◽  
Suck-Ku Kang
Keyword(s):  
Conjugate Addition ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Active Methylene Compounds ◽  
Active Methylene

Lewis Acid Activation of Pyridines for Nucleophilic Aromatic Substitution and Conjugate Addition

ChemSusChem ◽  
2015 ◽  
Vol 8 (6) ◽  
pp. 1083-1087 ◽  
Author(s):  
Sarah Abou-Shehada ◽  
Matthew C. Teasdale ◽  
Steven D. Bull ◽  
Charles E. Wade ◽  
Jonathan M. J. Williams
Keyword(s):  
Lewis Acid ◽  
Conjugate Addition ◽  
Nucleophilic Aromatic Substitution ◽  
Acid Activation ◽  
Aromatic Substitution

Concise Synthesis of Furo[2,3-b]indolines via [3,3]-Sigmatropic Rearrangement of N-Alkenyloxyindoles

Synlett ◽  
2020 ◽  
Author(s):  
Laura L. Anderson ◽  
Michael Shevlin ◽  
Neil A. Strotman
Keyword(s):  
High Throughput ◽  
Conjugate Addition ◽  
Sigmatropic Rearrangement ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Synthetic Route ◽  
High Throughput Experimentation ◽  
Activated Alkynes

A concise new synthetic route to furo[2,3-b]indolines has been developed by taking advantage of the reactivity of N-alkenyloxyindole intermediates. These compounds spontaneously undergo [3,3]-sigmatropic rearrangement followed by cyclization to form hemiaminals as single diastereomers. Tin-promoted N-hydroxyindole formation followed by conjugate addition to activated alkynes provides simple and modular access to a diverse array of N-alkenyloxyindoles and their corresponding furo[2,3-b]indolines. Microscale high-throughput experimentation was used to facilitate investigation of the scope and tolerance of this transformation and related studies on the nucleophilic aromatic substitution and rearrangement of N-hydroxyindoles with halogenated arenes have also been evaluated.

ChemInform Abstract: Lewis Acid Activation of Pyridines for Nucleophilic Aromatic Substitution and Conjugate Addition.

ChemInform ◽  
2015 ◽  
Vol 46 (30) ◽  
pp. no-no
Author(s):  
Sarah Abou-Shehada ◽  
Matthew C. Teasdale ◽  
Steven D. Bull ◽  
Charles E. Wade ◽  
Jonathan M. J. Williams
Keyword(s):  
Lewis Acid ◽  
Conjugate Addition ◽  
Nucleophilic Aromatic Substitution ◽  
Acid Activation ◽  
Aromatic Substitution

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.

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