Iron-catalyzed cross-dehydrogenative C N coupling of thiohydantoins with various amines

Mudaliar, Sulochana S.; Patel, Anuj P.; Patel, Janki J.; Chikhalia, Kishor H.

doi:10.1016/j.tetlet.2018.01.024

Cited by 12 publications

(4 citation statements)

References 42 publications

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“…[211] Recently, Chikhalia et al reported a novel method for synthesizing N-substituted amines from Fe-catalyzed C(sp 3 )À H/NÀ H bond CDC reaction between various thiohydantoins and amine derivatives by employing the oxidant TBHP under optimal conditions (Scheme 102). [212] A plausible mechanism for Fe-catalyzed C(sp 3 )À H/NÀ H CDC of thiohydantoins with amines was proposed (Scheme 103). The reaction mechanism was initiated by the oxidation of Fe II catalyst with TBHP to give Fe III complex and the formation of tert-butoxy radical.…”

Section: Fe-catalyzed C(sp 3 )à H Aminationmentioning

confidence: 99%

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Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

et al. 2022

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The progress in CÀ N bond construction is significant in synthetic and biological chemistry. Cross-dehydrogenative couplings of CÀ H and NÀ H motifs serve as a unique class of the most atom-economical and straightforward strategies for constructing CÀ N bonds. Herein, we enclosed the most updated methodologies developed in the assembly of CÀ N bonds via photo-catalyzed, transition-metal-catalyzed, electrochemical, and metal-free amination and amidation reactions of saturated and unsaturated CÀ H bonds. Compared with the well-established transition-metal-catalyzed protocols, electricity, or visible light-mediated amination and amidation reactions are competent and appealing. Plausible mechanistic pathways are also described in representative amidation and amination reactions to provide insights for the future development of environmentally kind processes.

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Section: Fe-catalyzed C(sp 3 )à H Aminationmentioning

confidence: 99%

“…reported a novel method for synthesizing N ‐substituted amines from Fe‐catalyzed C(sp 3 )−H/N−H bond CDC reaction between various thiohydantoins and amine derivatives by employing the oxidant TBHP under optimal conditions (Scheme 102). [212] …”

Section: C−h Bond Aminationmentioning

confidence: 99%

Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

et al. 2022

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“…The addition of TEMPO to the α-carbon of arylacetic acids is shown in Scheme b, which is proposed to be formed through the addition of TEMPO to an iron enolate with concomitant reduction of the iron catalyst . The iron-catalyzed α-amination of thiohydantoins is shown in Scheme c, which is proposed to proceed through an α-carbocation, stabilized by the adjacent nitrogen in the ring . To the best of our knowledge, this α-amination of thiohydantoins is the only previous report of iron-catalyzed direct α-amination of carbonyl compounds.…”

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confidence: 96%

“…16 The iron-catalyzed α-amination of thiohydantoins is shown in Scheme 1c, which is proposed to proceed through an αcarbocation, stabilized by the adjacent nitrogen in the ring. 17 To the best of our knowledge, this α-amination of thiohydantoins is the only previous report of iron-catalyzed direct α-amination of carbonyl compounds. This work comprises the identification of conditions for the α-amination of ketones directly with free sulfonamides in the presence of iron halide salts and quinone-based oxidants (Scheme 1d).…”

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confidence: 99%

Iron-Catalyzed Oxidative α-Amination of Ketones with Primary and Secondary Sulfonamides

Song

2023

J. Org. Chem.

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Iron‐Catalyzed Cross‐Dehydrogenative Coupling

Fan¹,

Li²

2022

Handbook of CH-Functionalization

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The sustainable construction of carbon–carbon bonds or carbon–heteroatom bonds is critical for future green chemical synthesis. Cross‐dehydrogenative coupling (CDC) reactions have thus been widely developed as one of the most sustainable and efficient synthetic strategies for such a philosophy. A number of obvious merits of iron catalysts make this reaction model more potential for industrial production and manufacturing applications. Iron‐catalyzed CDC reactions have emerged as a greener strategy for the direct formation of CC and C–heteroatom bonds from easily available compounds. The use of simple, low toxicity, and cheap iron‐based catalysts meets the criteria for the basis of chemical synthesis compared to those high price, toxic, and precious metal catalysts. In this article, we present the development of iron‐catalyzed CDC reactions by some selected results.

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Iron-catalyzed cross-dehydrogenative C N coupling of thiohydantoins with various amines

Cited by 12 publications

References 42 publications

Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

Iron-Catalyzed Oxidative α-Amination of Ketones with Primary and Secondary Sulfonamides

Iron‐Catalyzed Cross‐Dehydrogenative Coupling

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