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Enolate Anions and Condensation Reactions
Published in Michael B. Smith, A Q&A Approach to Organic Chemistry, 2020
Since the α-proton is a weak acid, the base used to remove that proton must be rather strong. A variety of bases can be used, including NaOEt, NaOH, NaOMe, KOt-OBu, and amide bases such as NaNH2, NaNR2 LiNH2, and LiNR2. Note that the conjugate acids of all of these bases (EtOH, MeOH, NH3, R2NH, etc.) are relatively weak acids, weaker than the α-proton of a ketone or aldehyde. What are “non-nucleophilic” bases?
Assessment of amination reactions via nucleophilic aromatic substitution using conventional and eco-friendly energies
Published in Green Chemistry Letters and Reviews, 2018
Ricardo A. Luna-Mora, Ángeles Torres-Reyes, Oscar A. González-Cruz, Fernando Ortega-Jiménez, Hulme Ríos-Guerra, Jessica V. González-Carrillo, Francisco Barrera-Téllez, Javier Perez-Flores, José G. Penieres-Carrillo
In the same way, when the binucleophile 2-aminoethanol 2c was reacted with 1a in the presence of a strong non-nucleophilic base (entry 2), N-(5-(2-hydroxyethylamino)-2-nitrophenyl)acetamide 3c was isolated as the unique product in good yield without the formation of N-(5-(2-aminoethoxy)-2-nitrophenyl)acetamide. This outcome suggested that the reactivity by orbital control instead of charge control, apart from the easy of stabilization (12) of δL-complex I might be ruled.
A review on DBU-mediated organic transformations
Published in Green Chemistry Letters and Reviews, 2022
Shashi Kanth Boddu, Najeeb Ur Rehman, Tapan Kumar Mohanta, Anjoy Majhi, Satya Kumar Avula, Ahmed Al-Harrasi
The notable advantages of DBU to be used in many organic reactions as it is less expensive, commercially readily available, homogenous, easy to handle, and most importantly recoverable. The benefit of the DBU catalyst has been explored for the practical methodologies useful for the synthesis of a wide variety of organic materials. In recent years, DBU has been used as a nucleophilic/non-nucleophilic base, catalyst, and complexing ligand and in many organic reactions.