In situ co-activation–nucleophilic aromatic substitution (ISCA–S N Ar): synthesis of α-aryl-α-heteroarylmalononitriles
Open Access
- 1 January 2026
- journal article
- Published by Royal Society of Chemistry (RSC) in Chemical Science
Abstract
We report that the direct mixing of α-arylmalononitriles and haloheterocycles triggers in situ co-activation (ISCA) to generate a reactive carbanion and pyridinium ion pair for nucleophilic aromatic substitution (S N Ar).Keywords
Funding Information
- National Institute of General Medical Sciences (R35GM137893)
- University of Minnesota
This publication has 75 references indexed in Scilit:
- Cobalt‐Catalyzed Decarboxylative Allylations: Development and Mechanistic StudiesChemistry – A European Journal, 2023
- Implicit solvation in domain based pair natural orbital coupled cluster (DLPNO‐CCSD) theoryJournal of Computational Chemistry, 2021
- Concerted Nucleophilic Aromatic Substitution ReactionsAngewandte Chemie International Edition, 2019
- C−H Cyanation of 6‐Ring N‐Containing HeteroaromaticsChemistry – A European Journal, 2017
- On the Basicity of Conjugated Nitrogen Heterocycles in Different MediaEuropean Journal of Organic Chemistry, 2017
- Effect of Substituents in the Syntheses of Phenyl‐Substituted DibenzonaphthyridinesJournal of Heterocyclic Chemistry, 2013
- Aliphatic Substitution: Nucleophilic and Organometallic2006
- Aromatic Substitution, Nucleophilic and Organometallic2006
- Equilibrium acidities and homolytic bond dissociation enthalpies of the acidic C-H bonds in dialkyl malonates and related compoundsJournal of Physical Organic Chemistry, 1994
- A malonic ester‐type synthesis with 4‐chloroquinoline utilizing highly acidic enolsJournal of Heterocyclic Chemistry, 1977