Efficient Amination of Activated and Non‐Activated C(sp<sup>3</sup>)−H Bonds with a Simple Iron–Phenanthroline Catalyst

Jarrige, Lucie; Zhou, Zijun; Hemming, Marcel; Meggers, Eric

doi:10.1002/ange.202013687

Cited by 4 publications

(5 citation statements)

References 69 publications

(18 reference statements)

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“…[41][42][43][44][45][46][47][48][49][50][51][52][53] Recently, we discovered dioxazolones can undergo intermolecular N-N coupling with arylamines to make hydrazides under either iridium or iron catalysis. [54][55][56][57][58][59][60][61][62][63][64] Mechanistic studies of the Ir-catalyzed system indicated an outer-sphere nucleophilic attack of the nitrogen group of Ir-nitrenoid intermediate by amine leads to the N-N coupling product.…”

Section: Resultsmentioning

confidence: 99%

Nitrene-Mediated P–N Coupling Under Iron Catalysis

et al. 2022

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P-N and P=N bonds play important roles in the design and synthesis of functional molecules such as bioactive compounds and organic ligands for catalysis. Existing methods for P-N coupling mostly rely on Staudinger condensation or nucleophilic substitution between phosphorus electrophiles and amine nucleophiles. Herein, we report a nitrene-mediated intermolecular P-N coupling reaction between various phosphorus nucleophiles and dioxazolones under simple iron-catalyzed conditions. These reactions offer an efficient, versatile, and broadly applicable method for synthesis of a range of N-P compounds including amidophosphines, iminophosphonamides, phosphinamides, aminophosphines, and iminophosphoranes from readily available precursors under mild conditions.

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Section: Resultsmentioning

confidence: 99%

Nitrene-Mediated P–N Coupling Under Iron Catalysis

et al. 2022

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“…2‐Imidazolidones 17 , which are the key scaffolding in bioactive chemicals, have been synthesized using N‐benzoyloxyureas 16 and ferrous chloride as a catalyst [45]. The C–H amination of propargylic and allylic C(sp 3 )–H bonds were effectively converted into 2‐imidazolidones respectively.…”

Section: Intramolecular Cyclization Methods For N‐heterocycle Synthesismentioning

confidence: 99%

“…catalyst [45]. The C-H amination of propargylic and allylic C(sp 3 )-H bonds were effectively converted into 2-imidazolidones respectively.…”

Section: °Cmentioning

confidence: 99%

Iron‐catalyzed intermolecular and intramolecular cyclization reactions of N‐heterocycles

Kaushik,

Jain,

Kishore

et al. 2024

Journal of Heterocyclic Chem

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N‐Heterocyclic compounds have been appealing pharmacophores in their use as drug production substrates. In this review paper, the cyclization of N‐heterocycles, using iron as a catalyst, and their mechanistic pathways have been highlighted and presented comprehensively. This paper will provide researchers with in‐depth knowledge of their approach to synthesis by employing a greener way rather than a conventional one. The present review firmly establishes that iron catalysts by their innate ability and inherent potential to acquire the four oxidation states coupled with their easy accessibility, inexpensive, and environment‐friendly nature have remained the mainstay in chemistry as the evergreen catalyst in the domain of organic synthesis. This review paper extensively explores iron‐catalyzed cyclization of N‐heterocycles, elucidating mechanistic pathways and emphasizing greener synthesis methods. Iron's versatility, accessibility, and eco‐friendliness solidify its position as a cornerstone in organic synthesis.

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“…In 2021, Eric and coworkers reported a robust protocol for the synthesis of cyclic amides 188 from direct C(sp 3 )−H amidation of benzylic, allylic, propargylic, and completely non‐activated aliphatic C(sp 3 )−H bonds 187 using a simple iron salt in combination with a readily available ligand under mild conditions (Scheme 48). [68] They commenced the optimization study by selecting N‐benzoyloxyurea as a model substrate. This revealed that 10 mol % FeCl 2 .4H 2 O as a catalyst, 3.0 equiv.…”

Section: Iron Catalyzed C(sp3)−h Functionalization Reactionsmentioning

confidence: 99%

The Recent Advances in Iron‐Catalyzed C(sp³)−H Functionalization

Bhavyesh,

Soliya,

Konakanchi

et al. 2024

Chemistry An Asian Journal

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The use of iron as a core metal in catalysis has become a research topic of interest over the last few decades. The reasons are clear. Iron is the most abundant transition metal on Earth’s crust and it is widely distributed across the world. It has been extracted and processed since the dawn of civilization. All these features render iron a noncontaminant, biocompatible, nontoxic, and inexpensive metal and therefore it constitutes the perfect candidate to replace noble metals (rhodium, palladium, platinum, iridium, etc.). Moreover, direct C–H functionalization is one of the most efficient strategies by which to introduce new functional groups into small organic molecules. The majority of organic compounds contain C(sp3)–H bonds. Given the enormous importance of organic molecules in so many aspects of existence, the utilization and bioactivity of C(sp3)–H bonds are of the utmost importance. This review sheds light on the substrate scope, selectivity, benefits, and limitations of iron catalysts for direct C(sp3)–H bond activations. An overview of the use of iron catalysis in C(sp3)–H activation protocols is summarized herein up to 2022.

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Efficient Amination of Activated and Non‐Activated C(sp³)−H Bonds with a Simple Iron–Phenanthroline Catalyst

Cited by 4 publications

References 69 publications

Nitrene-Mediated P–N Coupling Under Iron Catalysis

Nitrene-Mediated P–N Coupling Under Iron Catalysis

Iron‐catalyzed intermolecular and intramolecular cyclization reactions of N‐heterocycles

The Recent Advances in Iron‐Catalyzed C(sp³)−H Functionalization

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Efficient Amination of Activated and Non‐Activated C(sp3)−H Bonds with a Simple Iron–Phenanthroline Catalyst

Cited by 4 publications

References 69 publications

Nitrene-Mediated P–N Coupling Under Iron Catalysis

Nitrene-Mediated P–N Coupling Under Iron Catalysis

Iron‐catalyzed intermolecular and intramolecular cyclization reactions of N‐heterocycles

The Recent Advances in Iron‐Catalyzed C(sp3)−H Functionalization

Contact Info

Product

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Efficient Amination of Activated and Non‐Activated C(sp³)−H Bonds with a Simple Iron–Phenanthroline Catalyst

The Recent Advances in Iron‐Catalyzed C(sp³)−H Functionalization