Visible light mediated iron-catalyzed addition of oxamic acids to imines

Badufle, Margaux; Robert, Frédéric; Landais, Yannick

doi:10.1039/d4ra02258k

Cited by 5 publications

(2 citation statements)

References 60 publications

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“…In another case, the same group reported a decarboxylative addition of the oxamic acids to imines under the similar reaction conditions (Scheme 13b). 21 Mechanistically, the carbamoyl radical directly added to an acid-activated imine to offer a cation radical, followed by reduction and protonation to give the final product. The oxamic acids with various alkyl or aryl groups were well tolerated.…”

Section: Lmct Of Carboxylate-iron Species In Organic Synthesismentioning

confidence: 99%

“…Over the last five years, LMCT of iron species has been developed substantially and applied to different kinds of organic transformations. 1 f ,6–30 These studies are mainly based on LMCT of Fe( iii )-Cl and Fe( iii )-OR species. A chloride radical, which is a well-known hydrogen atom transfer (HAT) agent, can be produced in LMCT of Fe( iii )-Cl species.…”

Section: Introductionmentioning

confidence: 99%

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Light-induced ligand-to-metal charge transfer of Fe(iii)-OR species in organic synthesis

Qin,

Lei,

Gao

et al. 2024

Org. Biomol. Chem.

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Section: Lmct Of Carboxylate-iron Species In Organic Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Light-induced ligand-to-metal charge transfer of Fe(iii)-OR species in organic synthesis

Qin,

Lei,

Gao

et al. 2024

Org. Biomol. Chem.

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Copper‐Mediated Synthesis of N‐Aryl‐Oxamic Acids

Badufle,

Robert,

Landais

2024

Chemistry A European J

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The Cu‐catalyzed Ullmann‐Goldberg cross‐coupling between aryl iodides and oxamates is shown to afford the corresponding N‐aryloxamates with yields ranging from moderate to excellent, when the oxamate precursor incorporates a bulky tertiary alkyl group effectively preventing product degradation under the strongly basic reaction conditions. The final oxamic acids are then generated through the acid hydrolysis of the oxamate in high yields. These acids were then converted into urethanes using PIDA under thermal conditions or a visible‐light Fe‐LMCT process. While electron‐deficient N‐aryl oxamic acids provide urethanes with high efficiencies, electron‐rich counterparts led to diminished yields due to aryl group over‐oxidation induced by PIDA.

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Iron-Catalyzed Multicomponent C–H Alkylation of in Situ Generated Imines via Photoinduced Ligand-to-Metal Charge Transfer

Li,

Tu,

et al. 2024

Org. Lett.

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Herein, we describe a novel photoinduced iron-catalyzed strategy for multicomponent C−H alkylation of in situ generated imines. By utilizing the alkyl radicals generated through iron-mediated photocatalytic C−H activation, the imines formed in situ are further subjected to addition reactions, resulting in the synthesis of various secondary and tertiary amine products. This method is simple to operate and does not require additional oxidants. It is applicable to inert alkane substrates such as cyclic alkanes, cyclic ethers, toluene, and ketones. The reaction is also compatible with various aromatic amines, alkyl amines, halogenated aromatic amines, as well as aromatic aldehydes, alkyl aldehydes, and cinnamaldehyde, among other different types of aldehydes.

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Visible light mediated iron-catalyzed addition of oxamic acids to imines

Abstract: Oxamic acids where shown to add to imines, providing a broad range of α-aminoacid amides in generally good yields.

Cited by 5 publications

References 60 publications

Light-induced ligand-to-metal charge transfer of Fe(iii)-OR species in organic synthesis

Light-induced ligand-to-metal charge transfer of Fe(iii)-OR species in organic synthesis

Copper‐Mediated Synthesis of N‐Aryl‐Oxamic Acids

Iron-Catalyzed Multicomponent C–H Alkylation of in Situ Generated Imines via Photoinduced Ligand-to-Metal Charge Transfer

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