Synthesis of Amidines from Amides Using a Nickel‐Catalyzed Decarbonylative Amination through CO Extrusion Intramolecular Recombination Fragment Coupling

Liu, Xiangqian; Yue, Huifeng; Jia, Jiaqi; Guo, Lin; Rueping, Magnus

doi:10.1002/chem.201702867

Cited by 52 publications

(20 citation statements)

References 82 publications

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“…As for the future, the recent study on cooperative catalytic decarbonylative cross‐coupling of N , N ‐di‐Boc 2 amides is noteworthy as it demonstrates how to circumvent high energy, unstable intermediates, and do so while using practical, primary‐amide‐derived precursors . We fully expect that the tremendous advantages imparted by the N ‐acyl‐glutarimide scaffold will lead to the development of novel decarbonylative cross‐couplings that are beyond the scope of other acyl electrophiles …”

Section: Evaluation Of Utility In Organic Synthesismentioning

confidence: 99%

N‐Acyl‐Glutarimides: Privileged Scaffolds in Amide N–C Bond Cross‐Coupling

2018

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In this Microreview, we describe the recent exciting developments in the burgeoning area of amide N–C cross‐coupling enabled by amide bond twist of N‐acyl‐glutarimides. Since the initial reports in 2015, these amides have been demonstrated to be by far the most reactive amide derivatives in the biologically‐relevant manifold of N–C activation/cross‐coupling, thus stimulating the development of more than 10 previously unknown catalytic modes of reactivity of the amide bond. The capacity of N‐acyl‐glutarimides as privileged scaffolds to expedite acyl and decarbonylative cross‐couplings by amide N–C cleavage is discussed.

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Section: Evaluation Of Utility In Organic Synthesismentioning

confidence: 99%

N‐Acyl‐Glutarimides: Privileged Scaffolds in Amide N–C Bond Cross‐Coupling

2018

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“…In 2017, Rueping and co‐workers reported a nickel‐catalyzed decarbonylative amination reaction that proceeded through CO extrusion with intramolecular fragment coupling (Scheme ) . Extensive optimization was performed with various nickel catalysts, ligands, and solvents, and their optimal conditions used NiCl 2 /IPr ⋅ HCl with K 3 PO 4 (2.0 equiv) in toluene at 170 °C.…”

Section: Reactions Of Amides Through N−c Activationmentioning

confidence: 99%

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Chaudhari

Gnanaprakasam

2018

Chemistry An Asian Journal

134

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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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“…Since a number of reliable methods are available for amide formation,6,7 the key issue is the development of the latter decarbonylation reaction. Except for 2-azinecarboxamides,8 catalytic decarbonylation of amides is an unattained transformation, indicating that C(aryl)–N bond formation via decarbonylation is clearly not a trivial task. We report herein on the realization of this objective.…”

Section: Introductionmentioning

confidence: 99%