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Synthesis 2020; 52(18): 2579-2599
DOI: 10.1055/s-0040-1707101
DOI: 10.1055/s-0040-1707101
review
Non-Classical Amide Bond Formation: Transamidation and Amidation of Activated Amides and Esters by Selective N–C/O–C Cleavage
The National Science Foundation (CAREER CHE-1650766) is gratefully acknowledged for supportFurther Information
Publication History
Received: 26 February 2020
Accepted after revision: 27 March 2020
Publication Date:
15 May 2020 (online)
Abstract
In the past several years, tremendous advances have been made in non-classical routes for amide bond formation that involve transamidation and amidation reactions of activated amides and esters. These new methods enable the formation of extremely valuable amide bonds via transition-metal-catalyzed, transition-metal-free, or metal-free pathways by exploiting chemoselective acyl C–X (X = N, O) cleavage under mild conditions. In a broadest sense, these reactions overcome the formidable challenge of activating C–N/C–O bonds of amides or esters by rationally tackling nN → π*C=O delocalization in amides and nO → π*C=O donation in esters. In this account, we summarize the recent remarkable advances in the development of new methods for the synthesis of amides with a focus on (1) transition-metal/NHC-catalyzed C–N/C–O bond activation, (2) transition-metal-free highly selective cleavage of C–N/C–O bonds, (3) the development of new acyl-transfer reagents, and (4) other emerging methods.
1 Introduction
2 Transamidation of Amides
2.1 Transamidation by Metal–NHC Catalysis (Pd–NHC, Ni–NHC)
2.2 Transition-Metal-Free Transamidation via Tetrahedral Intermediates
2.3 Reductive Transamidation
2.4 New Acyl-Transfer Reagents
2.5 Tandem Transamidations
3 Amidation of Esters
3.1 Amidation of Esters by Metal–NHC Catalysis (Pd–NHC, Ni–NHC)
3.2 Transition-Metal-Free Amidation of Esters via Tetrahedral Intermediates
3.3 Reductive Amidation of Esters
4 Transamidations of Amides by Other Mechanisms
5 Conclusions and Outlook
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For representative reviews on amide bond formation, see:
For a recent review on transamidations, see:
For a classic amidation of esters using aluminum amides, see:
For a recent example of a hydroxy-directed amidation of esters, see:
For a recent example of catalytic amidation using TFE as a promoter, see:
For representative reviews on N–C bond activation, see:
For selected studies on activation of amide bonds, see:
For selected studies on amide bond destabilization pertinent to N–C activation, see:
For selected reviews on Pd–NHC catalysis, see:
For the early report on N-acyl-saccharins in N–C cross-coupling, see:
For recent elegant applications of opening of this class of bridged lactams in polymerization, see:
For cooperative catalysis in acyl N–C cross-coupling, see:
For cooperative catalysis in decarbonylative N–C cross-coupling, see:
See also: