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Updated: Feb 5, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Transition-Metal-Free Esterification of Amides via Selective N-C Cleavage under Mild Conditions
Guangchen Li1, Peng Lei1,2, Michal Szostak1
1Department of Chemistry , Rutgers University , 73 Warren Street , Newark , New Jersey 07102 , United States.
Abstract:
A general, transition-metal-free, and operationally simple method for esterification of amides by a highly selective cleavage of N-C(O) bonds under exceedingly mild conditions is reported. The reaction is characterized by broad substrate scope and excellent functional group tolerance. The potential of this mild esterification is highlighted by late-stage diversification of natural products and pharmaceuticals. Conceptually, the metal-free acyl functionalization of amides represents a significant step forward as a practical alternative to ligand exchange in acylmetal intermediates.
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Properties of Transition Metals
Cleavage and Blastulation
Phase Transitions
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Phase Transitions: Vaporization and Condensation
Phase Transitions: Sublimation and Deposition