Metal‐Catalyzed Oxidative C−H Bond Functionalization of 1,4‐Benzoxazinones

Kumar, Shankar; Ravi, Rangnath; Sahu, Tanu; Jha, Vikesh Kumar; Baweja, Renu; Jha, Abadh Kishor

doi:10.1002/ajoc.202400028

Asian J Org Chem

2024

DOI: 10.1002/ajoc.202400028

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Metal‐Catalyzed Oxidative C−H Bond Functionalization of 1,4‐Benzoxazinones

Shankar Kumar,

Rangnath Ravi,

Tanu Sahu

et al.

Abstract: Abstract.The present review shows metal‐catalyzed oxidative C(sp3)‐H/C(sp2)‐H bond functionalization of 1,4‐benzoxazinones by utilizing various substrates such as indoles, phosphites or phosphine oxides, malonate esters, and resorcinol, which lead to the formation of new C‐C or C‐P bonds. The metal catalysts used for these couplings include Fe, Cu, Ag, and Ru. This follows a strategy involving either the one‐electron oxidation process (OEO), ball milling technique, or photocatalytic process. The synthesized pr… Show more

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Cited by 3 publications

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Metal‐Catalyzed Coupling of N‐Tosylhydrazones with Compounds Containing C−H/Heteroatom‐H Bonds

Akanksha,

Singh,

Asthana

et al. 2024

Asian J Org Chem

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The present review covers various advances in the field of metal‐catalyzed coupling of N‐tosylhydrazones with compounds containing C‐H/heteroatom‐H bonds, including transition metal catalysts i.e., Pd, Rh, Cu, Ag, Ni and Co and resulting alkylated, alkenylated, alkynylated, allenylated, annulated and many other products. A metal carbene migratory insertion process play a key role in carbon‐carbon single bond (C‐C) and carbon‐carbon double bond (C=C) formation and undergoes variety of cascade reactions to synthesize a wide scope of pharmaceutically and medicinally valuable scaffoldings.

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Metal‐Catalyzed Coupling of N‐Tosylhydrazones with Compounds Containing C−H/Heteroatom‐H Bonds

Akanksha,

Singh,

Asthana

et al. 2024

Asian J Org Chem

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Pioneering Metal‐Free Late‐Stage C−H Functionalization Using Acridinium Salt Photocatalysis

Kanti Bera,

Porcheddu

2024

Chemistry A European J

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Using organic dyes as photocatalysts is an innovative approach to photocatalytic organic transformations. These dyes offer advantages such as widespread availability, adaptable absorption properties, and diverse chemical structures. Recent progress has led to the development of organic photocatalysts that can utilize visible light to modify chemically inert C‐H bonds. These catalysts are sustainable, selective, and versatile, enabling mild reactions, late‐stage functionalization, and various transformations in line with green chemistry principles. As catalysts in photoredox chemistry, they contribute to the development of efficient and environmentally friendly synthetic pathways. Acridinium‐based organic photocatalysts have proved valuable in late‐stage C‐H functionalization, enabling transformative reactions under mild conditions. This review emphasizes their innovative features, such as organic frameworks, efficient light absorption properties, and their applications in modifying complex molecules. It provides an overview of recent advancements in the use of acridinium‐based organic photocatalysts for late‐stage C‐H bond functionalization without the need for transition metals, showcasing their potential to expedite the development of new molecules and igniting excitement about the prospects of this research in the field.

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Synthesis and Ligand Properties of Silsesquioxane‐Caged Phosphite T₇Ph₇P

Hunsicker,

Krebs,

Zimmer

et al. 2024

Zeitschrift anorg allge chemie

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The synthesis of the phosphorus‐capped heptaphenylsilsesquioxane T7Ph7P is reported. We show that, unlike previous examples, it readily forms Lewis acid‐base adducts with boranes of different steric demand and the FeCO4 fragment. All complexes were characterized by multinuclear NMR and IR spectroscopy in solution and the solid state. The molecular structures of the adducts with BPh3 and B(C6F5)3 were determined from XRD suitable single crystals. The relative conformation of the Ph and C6F5 rings in T7Ph7P‐B(C6F5)3 suggests favorable π‐interactions, stabilizing the adducts to such a degree that attempts to activate H2 or CO2 were unsuccessful.

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Metal‐Catalyzed Oxidative C−H Bond Functionalization of 1,4‐Benzoxazinones

Cited by 3 publications

References 66 publications

Metal‐Catalyzed Coupling of N‐Tosylhydrazones with Compounds Containing C−H/Heteroatom‐H Bonds

Metal‐Catalyzed Coupling of N‐Tosylhydrazones with Compounds Containing C−H/Heteroatom‐H Bonds

Pioneering Metal‐Free Late‐Stage C−H Functionalization Using Acridinium Salt Photocatalysis

Synthesis and Ligand Properties of Silsesquioxane‐Caged Phosphite T₇Ph₇P

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Metal‐Catalyzed Oxidative C−H Bond Functionalization of 1,4‐Benzoxazinones

Cited by 3 publications

References 66 publications

Metal‐Catalyzed Coupling of N‐Tosylhydrazones with Compounds Containing C−H/Heteroatom‐H Bonds

Metal‐Catalyzed Coupling of N‐Tosylhydrazones with Compounds Containing C−H/Heteroatom‐H Bonds

Pioneering Metal‐Free Late‐Stage C−H Functionalization Using Acridinium Salt Photocatalysis

Synthesis and Ligand Properties of Silsesquioxane‐Caged Phosphite T7Ph7P

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Product

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Synthesis and Ligand Properties of Silsesquioxane‐Caged Phosphite T₇Ph₇P