Cerium Catalyzed Transamidation of Secondary Amides under Ultrasound Irradiation: A Breakthrough in Organic Synthesis

Mishra, Ankush; Singh, Sundaram; Srivastava, Vandana

doi:10.1002/ajoc.201800258

Cited by 19 publications

(12 citation statements)

References 35 publications

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“…Very recently,S rivastava and co-workers developed ac onvenient two-step approach fort he transamidation of secondary amides by using cerium as ac atalyst under ultrasound irradiation (Scheme 54). [107] In contrast with previous reports that used N-Boc or N-Tsg roups, the authors used N-COCF 3 -functionalized amides. Avariety of d-block metals were screened in the transamidationr eaction, with moderate success.…”

Section: Transamidation Reactionsmentioning

confidence: 99%

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Chaudhari

Gnanaprakasam

2018

Chemistry An Asian Journal

120

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The amide functional group is commonly found in peptides, proteins, pharmaceutical compounds, natural products, andp olymers.T he synthesis of amides is typically performed by using classical approaches that involvet he reaction between ac arboxylic acid and an amine in the presence of an activator.Amides are thought to be an inert functional group, because they are unsusceptible to nucleophile attack, owing to their low electrophilicity.T he reason fort his resistancei sc lear:t he resonance stability of the amide bond. However,t ransition metal catalysis can circumvent this stability by selectively rupturing the NÀCb ond of the amide, thereby facilitating further cross-couplingo ro ther reactions.Inthis Focus Review,wediscuss the recent advances in this area and present as ummary of methods that have been developed for activating the amide NÀCb ond by using precious and non-preciousmetals.

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Section: Transamidation Reactionsmentioning

confidence: 99%

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Chaudhari

Gnanaprakasam

2018

Chemistry An Asian Journal

120

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“…In 2018, Srivastava and co-workers reported the cerium-catalyzed transamidation of N-activated 2° amides under ultrasonic irradiation (Scheme 44). 69 In this intriguing method, they first activate 2° amides by introducing an electron-withdrawing trifluoroacetyl (TFA) group at the nitrogen atom. Treatment of N-TFA-activated amides with…”

Section: Transamidation Of Amides By Other Mechanismsmentioning

confidence: 99%

Non-Classical Amide Bond Formation: Transamidation and Amidation of Activated Amides and Esters by Selective N–C/O–C Cleavage

Szostak

2020

Synthesis

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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 Introduction2 Transamidation of Amides2.1 Transamidation by Metal–NHC Catalysis (Pd–NHC, Ni–NHC)2.2 Transition-Metal-Free Transamidation via Tetrahedral Intermediates2.3 Reductive Transamidation2.4 New Acyl-Transfer Reagents2.5 Tandem Transamidations3 Amidation of Esters3.1 Amidation of Esters by Metal–NHC Catalysis (Pd–NHC, Ni–NHC)3.2 Transition-Metal-Free Amidation of Esters via Tetrahedral Intermediates3.3 Reductive Amidation of Esters4 Transamidations of Amides by Other Mechanisms5 Conclusions and Outlook

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“…However, the use of activating reagents such as DCC, HATU, pyBOP, and HOBT in these reactions is not environmentally benign. [1] In this view, alternative methodologies, for example, hydrative amidation of alkynes, [2] transition metal catalysed aminative carbonylation of alkanes, [3] aryl halides [4] and alkynes, [5] azidation in Staudinger like reactions, [6] acylation of amines with esters, [7] transamidation [8] and Beckmann rearrangement, [9] etc., have also been successfully explored. In its continuation, direct amidation of the carbonyl function has gained much attention recently.…”

Section: Introductionmentioning

confidence: 99%

Visible‐Light Mediated Photooxidative Synthesis of α‐Keto Amides

2019

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Photocatalytic amidation of α-keto aldehydes is herein investigated. This transformation was achieved using rose bengal as photocatalyst at room temperature under ambient air and under irradiation of a 20 W white LED bulb. The method is mild, efficient and environmentally benign. This photocatalytic method is compatible with different unsubstituted and substituted α-keto aldehydes having electron-withdrawing or -donating groups, secondary amines, cyclic or acyclic, and primary aliphatic amines. Mechanistic studies reveal that the reaction proceeds via oxidative quenching of the photocatalyst.

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Cerium Catalyzed Transamidation of Secondary Amides under Ultrasound Irradiation: A Breakthrough in Organic Synthesis

Cited by 19 publications

References 35 publications

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Non-Classical Amide Bond Formation: Transamidation and Amidation of Activated Amides and Esters by Selective N–C/O–C Cleavage

Visible‐Light Mediated Photooxidative Synthesis of α‐Keto Amides

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