Visible‐light Induced Cerium‐catalyzed <i>N</i>‐Demethylation of <i>N</i>‐Methyl Amides under Air Conditions

Teng, Qing‐Hu; Sun, Greg; Fang-Ping, Huang; Wang, Kai; Liang, Fu‐Pei

doi:10.1002/adsc.202201176

Cited by 6 publications

(2 citation statements)

References 67 publications

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“…1 N-(4-(Trifluoromethyl)henyl)enzamide (2e). 20 (1:1 v/v, PE/EA) white solid, 87 mg, yield 65%. 1 N-(4-(Trifluoromethoxy)henyl)enzamide (2f).…”

Section: Mmol Scale Synthesis Of N-(4-chlorophenyl)benzamidementioning

confidence: 99%

Deoxygenative Hydroboration of Aromatic Nitro Compounds Catalyzed by Tetra(diisopropylamido) Rare-Earth Metal–Lithium Bimetallic Complexes

Chen,

Lu,

Zhao

2023

J. Org. Chem.

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The first example of the reduction of a nitro compound with HBPin catalyzed by tetra(diisopropylamido) rare-earth metal−lithium bimetallic complexes LiRE(N i Pr 2 ) 4 (THF) (RE = La, Nd, Sm, Gd, and Y) was disclosed. A series of aromatic nitro compounds were reduced to N-borylamines in high yields (up to 99%). The derivatives of N-borylamines�amides and carbamates�were obtained in a sequential one-pot manner. Furthermore, kinetic studies of the deoxygenative hydroboration of nitro compounds were carried out.

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“…1 N-(4-(Trifluoromethyl)henyl)enzamide (2e). 20 (1:1 v/v, PE/EA) white solid, 87 mg, yield 65%. 1 N-(4-(Trifluoromethoxy)henyl)enzamide (2f).…”

Section: Mmol Scale Synthesis Of N-(4-chlorophenyl)benzamidementioning

confidence: 99%

Deoxygenative Hydroboration of Aromatic Nitro Compounds Catalyzed by Tetra(diisopropylamido) Rare-Earth Metal–Lithium Bimetallic Complexes

Chen,

Lu,

Zhao

2023

J. Org. Chem.

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“…The reaction can selectively generate C–H arylation and N-dealkylation products through radical and cationic paths, respectively. In comparison to dealkylation of amine, the literature for amide dealkylation appears to be limited and seems more challenging. , Thus, a novel method specifically designed for both amine and amide dealkylation is of importance.…”

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confidence: 99%

Alkali-Driven Photoinduced N-Dealkylation of Aryl Tertiary Amines and Amides

Lian,

Chen,

Huang

et al. 2023

Org. Lett.

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By extending the photoinduced oxidative mechanism of aryl tertiary amines proposed earlier to an alkaline environment based on the prediction of quantum mechanics computations and the validation of meticulous experiments, we discovered a photoinduced oxidative N-dealkylation method for both aryl tertiary amines and amides. The dealkylation was achieved in an alkaline environment under mild conditions accompanied by excellent functional group tolerance.

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Iodine Mediated Annulation of Triethylamine, Aldehydes and 2‐Aminopyridines for the Synthesis of 3‐Formyl‐Imidazo [1,2‐a]pyridine Derivatives

Zhang,

Shen,

Zhang

2024

Adv Synth Catal

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With triethylamine as a synthon, an alternative method for the synthesis of 3‐formyl imidazo[1,2‐a]pyridines has been accomplished from aldehydes, and 2‐aminopyridines. The reaction proceeded via iodine‐catalyzed C−N bond cleavage of triethylamine, generation of α,β‐unsaturated aldehyde in situ, and oxidative cyclization with air as the oxygen source. This protocol may facilitate the synthesis of imidazo[1,2‐a]pyridine derivatives and provide a reference for the usage of triethylamine as a synthon.

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Visible‐light Induced Cerium‐catalyzed N‐Demethylation of N‐Methyl Amides under Air Conditions

Cited by 6 publications

References 67 publications

Deoxygenative Hydroboration of Aromatic Nitro Compounds Catalyzed by Tetra(diisopropylamido) Rare-Earth Metal–Lithium Bimetallic Complexes

Deoxygenative Hydroboration of Aromatic Nitro Compounds Catalyzed by Tetra(diisopropylamido) Rare-Earth Metal–Lithium Bimetallic Complexes

Alkali-Driven Photoinduced N-Dealkylation of Aryl Tertiary Amines and Amides

Iodine Mediated Annulation of Triethylamine, Aldehydes and 2‐Aminopyridines for the Synthesis of 3‐Formyl‐Imidazo [1,2‐a]pyridine Derivatives

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