Ni and Fe catalyzed cascade radical reactions of oxime esters with diselenides

Liu, Linpeng; Jian, Yanyu; Hu, Weigao; Zhao, Shaohu; Shi, Zhang‐Jie; Selander, Nicklas; Zhou, Taigang

doi:10.1039/d2qo00586g

Cited by 8 publications

(2 citation statements)

References 47 publications

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“…In 2022, Zhou’s group [ 53 ] carried out a nickel-and iron-catalyzed cascade free radical reaction of oxime esters with 69 . The author used aryl oxime esters 69-2 to react with 1,2-diphenyldiselane 70 to form pyrroline compounds 71-2 ( Figure 24 ), while for cycloketone oxime esters to react with 1,2-diphenyldiselane 70 to form alkyl nitriles 71-1 .…”

Section: The N-o Bond Cleavage Of Oximes To Construct N-heterocyclementioning

confidence: 99%

Recent Advances in N-O Bond Cleavage of Oximes and Hydroxylamines to Construct N-Heterocycle

et al. 2023

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Oximes and hydroxylamines are a very important class of skeletons that not only widely exist in natural products and drug molecules, but also a class of synthon, which have been widely used in industrial production. Due to weak N-O σ bonds of oximes and hydroxylamines, they can be easily transformed into other functional groups by N-O bond cleavage. Therefore, the synthesis of N-heterocycle by using oximes and hydroxylamines as nitrogen sources has attracted wide attention. Recent advances for the synthesis of N-heterocycle through transition-metal-catalyzed and radical-mediated cyclization classified by the type of nitrogen sources and rings are summarized. In this paper, the recent advances in the N-O bond cleavage of oximes and hydroxylamines are reviewed. We hope that this review provides a new perspective on this field, and also provides a reference to develop environmentally friendly and sustainable methods.

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Section: The N-o Bond Cleavage Of Oximes To Construct N-heterocyclementioning

confidence: 99%

Recent Advances in N-O Bond Cleavage of Oximes and Hydroxylamines to Construct N-Heterocycle

et al. 2023

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“…Selander, Zhou, and coworkers have reported a strategy to perform a radical cyclization and ring opening of oxime esters in the presence of diorganyl diselenides, with the process catalyzed by Ni(0) or Fe(II) species [71]. In this sense, the authors developed two methods to perform the synthetic transformations efficiently.…”

Section: Using Nickel As Catalystmentioning

confidence: 99%

Recent Approaches in Transition Metal-Catalyzed Chalcogenative Heteroannulation of Alkenes and Alkynes

Gutterres,

Anjos,

Santos

et al. 2023

Catalysts

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Organochalcogen-bearing heterocycles are important scaffolds in compounds under the spotlight of scientific interest in optoelectronic fields and for biological applications. The use of transition metals has been a versatile and reliable way to carry out the synthesis of these molecules efficiently, delivering products in high yields and with a wide functional diversity. In the last 10 years, many classes of heterocycles have been synthesized under the cyclization reaction of acyclic alkenes and alkynes with the incorporation of a chalcogen atom on its structure. Transition metal catalysts including Cu, Co, Pd, Ni, In, Ag, and Fe salts have been used in the development of new methodologies, the expansion of substrate scope, and mechanistic studies. This review provides an overview of these recent approaches with the aim of being a useful resource for interested researchers in this area.

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Electrochemical Selenylation‐Induced Annulation of Alkenyl Ureas to Access Cyclic Isoureas

Li,

Tang,

Zhou

et al. 2023

Adv Synth Catal

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A direct electrosynthesis of cyclic isoureas from N‐allyl ureas and diselenides has been described. This protocol proceeds without any additional catalyst and oxidant, at room temperature under air, providing the desired products in 71–91% yield. In addition, the synthesis of cyclic isoureas containing five to seven‐membered rings has also been achieved by the employment of this strategy. On the basis of the mechanism experiments and previous research works, a probable mechanism is proposed.

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Ni and Fe catalyzed cascade radical reactions of oxime esters with diselenides

Abstract: A radical cyclization and ring-opening of oxime esters with diselenides was developed. Both Ni(0) and Fe(II) catalysts could be employed for the selenylation of olefin-containing and cyclic oxime ester derivatives....

Cited by 8 publications

References 47 publications

Recent Advances in N-O Bond Cleavage of Oximes and Hydroxylamines to Construct N-Heterocycle

Recent Advances in N-O Bond Cleavage of Oximes and Hydroxylamines to Construct N-Heterocycle

Recent Approaches in Transition Metal-Catalyzed Chalcogenative Heteroannulation of Alkenes and Alkynes

Electrochemical Selenylation‐Induced Annulation of Alkenyl Ureas to Access Cyclic Isoureas

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