Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with <i>o</i>-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1<i>H</i>)-ones

Liu, Yongzhu; Qi, Xinxin; Wu, Xiao‐Feng

doi:10.1021/acs.joc.1c01984

Cited by 19 publications

(7 citation statements)

References 60 publications

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“…Although multiple methods have been explored for the construction of quinolin-2(1 H )-ones, the exploration of a novel approach for these significant N -heterocycles is a long-standing goal in synthetic and medicinal chemistry. In line with our previous work on the carbonylative synthesis of quinolin-2(1 H )-ones, we disclose here a cascade procedure for the access of 3-alkenylquinolin-2(1 H )-ones through a palladium-catalyzed reductive aminocarbonylation of o -iodophenol-derived allyl ethers. It is noteworthy that this is the first example on carbonylative synthesis of 3-alkenylquinolin-2(1 H )-ones from allylic ethers under mild reaction conditions.…”

supporting

confidence: 81%

Palladium-Catalyzed Reductive Aminocarbonylation of o-Iodophenol-Derived Allyl Ethers with o-Nitrobenzaldehydes to 3-Alkenylquinolin-2(1H)-ones

Liu

Wang

et al. 2022

Org. Lett.

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An attractive palladium-catalyzed reductive aminocarbonylation reaction of allylic ethers has been explored for the synthesis of 3-alkenylquinolin-2(1H)-one derivatives. With Mo-(CO) 6 as both CO surrogate and reductant, a variety of 3alkenylquinolin-2(1H)-ones were obtained in good to excellent yields from o-iodophenol-derived allyl ethers with o-nitrobenzaldehydes as the nitrogen sources. This reaction proceeds through a cascade pathway and does not rely on high-pressure CO gas as needed in former allylic carbonylation reactions. This strategy provides a new pathway for the construction of 3-alkenylquinolin-2(1H)-ones.

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confidence: 81%

Palladium-Catalyzed Reductive Aminocarbonylation of o-Iodophenol-Derived Allyl Ethers with o-Nitrobenzaldehydes to 3-Alkenylquinolin-2(1H)-ones

Liu

Wang

et al. 2022

Org. Lett.

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“…The authors have cited additional references within the Supporting Information. [47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62] 100010434), fellowship code LCF/BQ/PI18/11630023. R. A. and J. R. C.-A.…”

Section: General Procedures For Materials Preparationmentioning

confidence: 99%

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

2023

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An efficient heterogeneous silver‐catalyzed α‐alkylation of nitriles and oxindoles using alcohols via borrowing hydrogen strategy has been developed for the first time. The active nanostructured material, namely [Ag/Mg4Al‐LDH], composed by silver nanoparticles (3‐4 nm average particle size) homogeneously stabilized onto a [Mg4Al‐LDH] support with suitable Brönsted basic properties, constitutes a stable catalyst for the sustainable building of novel C‐C bonds from alcohols and C‐nucleophiles. By applying this catalyst, a broad range of α‐functionalized nitriles and oxindoles has been accessed with good to excellent isolated yields and without the addition of external bases. Moreover, the novel silver nanocatalyst has also demonstrated its successful application to the cyclization of N‐[2‐(hydroxymethyl)phenyl]‐2‐phenylacetamides to afford 3‐arylquinolin‐2(1H)‐ones, through a one‐pot dehydrogenation and intramolecular α‐alkylation. Control experiments, kinetic studies and characterization data of a variety of [Ag/LDH]‐type materials confirmed the silver role in the dehydrogenation and hydrogenation steps, while [Mg4Al‐LDH] matrix is able to catalyze condensation. Interestingly, these studies suggest as key point for the successful activity of [Ag/Mg4Al‐LDH], in comparison with other [Ag/LDH]‐type nanocatalysts, the suitable acid‐base properties of this material.

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“…The use of dimethylamine hydrochloride requires using a base restricting the reaction applicability. [18][19][20] This encouraged chemists to seek synthetic equivalents of this reagent.…”

Section: Introductionmentioning

confidence: 99%

Sodium hypophosphite mediated reductive amination of carbonyl compounds with N,N-dialkylformamides

et al. 2023

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Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1H)-ones

Cited by 19 publications

References 60 publications

Palladium-Catalyzed Reductive Aminocarbonylation of o-Iodophenol-Derived Allyl Ethers with o-Nitrobenzaldehydes to 3-Alkenylquinolin-2(1H)-ones

Palladium-Catalyzed Reductive Aminocarbonylation of o-Iodophenol-Derived Allyl Ethers with o-Nitrobenzaldehydes to 3-Alkenylquinolin-2(1H)-ones

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

Sodium hypophosphite mediated reductive amination of carbonyl compounds with N,N-dialkylformamides

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Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1H)-ones

Cited by 19 publications

References 60 publications

Palladium-Catalyzed Reductive Aminocarbonylation of o-Iodophenol-Derived Allyl Ethers with o-Nitrobenzaldehydes to 3-Alkenylquinolin-2(1H)-ones

Palladium-Catalyzed Reductive Aminocarbonylation of o-Iodophenol-Derived Allyl Ethers with o-Nitrobenzaldehydes to 3-Alkenylquinolin-2(1H)-ones

Silver Supported Nanoparticles on [Mg4Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

Sodium hypophosphite mediated reductive amination of carbonyl compounds with N,N-dialkylformamides

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Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols