Iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones toward functionalized pyridines

Duan, Jindian; Xu, Gaochen; Rong, Binsen; Yan, Huan; Zhang, Sai; Wu, Qinghuan; Zhu, Ning; Guo, Kai

doi:10.1016/j.gresc.2021.03.001

Cited by 29 publications

(15 citation statements)

References 78 publications

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“…The development of organometallic catalysis has had a tremendous impact on organic reaction and material synthesis during the past decades . To date, organometallic catalysis continues to shape the field, because it lies at the heart of many industrial processes producing bulk and fine chemicals. − Dirhodium carboxylates are bimetallic compounds with a lanternlike or paddle-wheel structure, which is composed of one Rh–Rh single bond, four bridging ligands, and two axial sites responsible for many of the complex stereoelectronic properties . By virtue of the unique structure and stability, these complexes led to many breakthroughs in catalysis, medicine, and electronic devices .…”

Section: Introductionmentioning

confidence: 99%

Self-Adaptive Dirhodium Complexes in a Metal–Organic Framework for Synthesis of N–H Aziridines

Jiang

Liu

et al. 2022

ACS Appl. Mater. Interfaces

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Conformational dynamics of active sites in enzymes enable great control over the catalytic process. Herein, we constructed a metal–organic framework with conformationally dynamic active sites (Rh2-ZIF-8). The active sites in Rh2-ZIF-8 were composed of the imidazolate-bridged bimetallic center with a catalytic dirhodium moiety and structural zinc site. Even though the coordination sphere of the dirhodium species was saturated with two circularly arranged esp groups and two axial 2-MeIm ligands, it could still effectively catalyze the direct synthesis of N–H aziridines from olefins with high activity. We found that such a self-adaptive catalytic process was based on the dynamic breakage and reformation of the rhodium–zinc imidazolate bridges. Interestingly, the in situ generated dirhodium site with a unique Rh2(esp)2(2-MeIm)1 configuration was able to exhibit obviously enhanced selectivity compared to homogeneous catalyst Rh2(esp)2. Furthermore, the surrounding zinc imidazolate groups could effectively protect the dirhodium moieties from harsh environments, and this ultimately endowed it with high stability.

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Section: Introductionmentioning

confidence: 99%

Self-Adaptive Dirhodium Complexes in a Metal–Organic Framework for Synthesis of N–H Aziridines

Jiang

Liu

et al. 2022

ACS Appl. Mater. Interfaces

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“…Over the past decades, transition-metal-catalyzed C–H bond cyclization reaction for the assembly of heterocyclic compounds have been extensively developed, which prove to be a powerful strategy with atom and step economy . Alkenes, alkynes, allenes, sulfoxonium ylides, and diazo compounds are frequently used as coupling partners. Nevertheless, it is inaccessible for building nonsubstituted compounds using these coupling partners, which has greatly limited its application in the synthesis of complex structural compounds.…”

mentioning

confidence: 99%

Rh(III)-Catalyzed Synthesis of Indazolo[2,3-a]quinolines: Vinylene Carbonate as C1 and C2 Building Blocks

et al. 2022

Org. Lett.

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A rhodium-catalyzed cyclization of azobenzenes and vinylene carbonate via C−H bond activation to construct indazolo[2,3-a]quinolines has been developed. This protocol offers an efficient method for synthesis of the titled products in good yields with broad functional group tolerance. In this reaction, three C−C bonds and C−N bond are formed in one pot, and vinylene carbonate (VC) acts as C1 and C2 synthons as well as "vinylene transfer" agent and acylation reagent in the construction of targetfused heterocycles. Moreover, the products exhibit favorable fluorescence properties, which indicate their potential application as fluorescent materials and biosensors.

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“…[15] To the best of our knowledge, the transformation of α,β-unsaturated ketoximes for the assembly of pyrimidines has never been documented. As part of our continued interest in oxime acetates, [16] we herein report an efficient iron-catalyzed homocoupling of α,β-unsaturated ketoximes for the synthesis of 2,4,6trisubstituted pyrimidines (Scheme 1f).…”

mentioning

confidence: 99%

“…Next screening of solvents clearly demonstrated that the homocoupling reaction was more efficient in DMSO/ 1,4-dioxane mixed solvents than in single solvent, and further investigation showed that the yield (73%) obtained from DMSO/1,4-dioxane (V/V = 1/5) solution was superior to those obtained using other ratios (entries [13][14][15]. Finally, the yield was negatively affected by either decreasing or increasing the reaction temperature (entries [16][17].…”

mentioning

confidence: 99%

Synthesis of 2,4,6‐Trisubstituted Pyrimidines via Iron‐Catalyzed Homocoupling of α,β‐Unsaturated Ketoximes

Guo

Wang

et al. 2022

Adv Synth Catal

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Iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones toward functionalized pyridines

Cited by 29 publications

References 78 publications

Self-Adaptive Dirhodium Complexes in a Metal–Organic Framework for Synthesis of N–H Aziridines

Self-Adaptive Dirhodium Complexes in a Metal–Organic Framework for Synthesis of N–H Aziridines

Rh(III)-Catalyzed Synthesis of Indazolo[2,3-a]quinolines: Vinylene Carbonate as C1 and C2 Building Blocks

Synthesis of 2,4,6‐Trisubstituted Pyrimidines via Iron‐Catalyzed Homocoupling of α,β‐Unsaturated Ketoximes

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