Copper-Mediated Oxidative Functionalization of C(sp<sup>3</sup>)–H Bonds with Isoquinolines: Two-Step Synthesis of 5-Oxaprotoberberinones

Wang, Dingyi; Zhang, Rongxing; Deng, Ruihong; Lin, Sen; Guo, Shengmei; Yan, Zhaohua

doi:10.1021/acs.joc.6b02145

Cited by 20 publications

(11 citation statements)

References 39 publications

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“…Recently, an interesting transformation of isoquinolines leading to N -benzylisoquinolin-1(2 H )-ones was demonstrated ( Scheme 47 ). 64 For this, 20 mol% of Cu 0 , Cu I (CuOAc, CuSCN, CuI, CuCl, CuBr and Cu 2 O) and CuBr 2 were tested in combination with 2 equiv. of ( t -BuO) 2 at 120 °C.…”

Section: Reactions Of Ethers With Heteroaromatic Compoundsmentioning

confidence: 99%

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Cross-dehydrogenative coupling and oxidative-amination reactions of ethers and alcohols with aromatics and heteroaromatics

2017

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Section: Reactions Of Ethers With Heteroaromatic Compoundsmentioning

confidence: 99%

“…With o -bromoanisole, this compound was 25% of the products formed whereas with p -bromoanisole it was 50% of the products formed. Formation of this product has been termed “competing exchange reaction” 64 by the authors.…”

Section: Reactions Of Ethers With Heteroaromatic Compoundsmentioning

confidence: 99%

Cross-dehydrogenative coupling and oxidative-amination reactions of ethers and alcohols with aromatics and heteroaromatics

2017

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“…Finally, the intermediate G by intermolecular rearragement form final product H and releasing iso ‐butylene (See Figure 3). [45] …”

Section: Copper Catalyzed Synthesis Of Heterocyclic Amidesmentioning

confidence: 99%

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Chandra

2021

ChemistrySelect

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Copper with variable oxidation states, Earth abundance was used as a tunable and multifunctional catalyst promoting organic transformations. Copper‐based catalytic materials have been effectively utilized in bioorganic chemistry, material science, and natural products synthesis. Several organic transformations involving cycloadditions, cyclizations, cross‐couplings, and condensations in one‐pot assist in the formation of multiple bonds like C−C/C−O bonds, C−C/C−N bonds, and C−N/C−S bonds. Copper has recently been explored as efficient catalytic material for the synthesis of heterocyclic amides. Heterocyclic amides are essential organic compounds are quite prevelent in the pharmaceuticals, fine chemicals and natural products. The heterocyclic amides are the key components of multivarious ace drugs and bio‐molecules like peptides and proteins, and several natural products. Therefore, heterocyclic amides are of much significance, and research focusing on the facile methods is of much interest to contemporary synthetic chemists. Different techniques have been developed using copper‐based catalysts for the synthesis of heterocyclic amdes. These heterocyclic amides are prepared by the reaction of C(sp3)−H, C(sp2)−H, C(sp)−H bonds, aldehydes, ketones, carboxylic acid, carboxylic acid‐based surrogates, and amine surrogates. N‐alkyation of amides with multifarious substrates has been the extensively investigated for the synthesis of heterocyclic amides. Finally, multicomponent domino reactions have also been investigated for the synthesis of heterocycic amides. The present review summarises various synthetic techniques for the copper catalyzed heterocyclic amides synthesis.

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“…In 2016 Lin, Yan and co‐workers studied the copper‐catalyzed functionalization of isoquinolines under oxidative conditions . The products of the reaction were C(sp 3 )−N derivatized isoquinolones, which are important structural components of many natural products and pharmaceutically active ingredients.…”

Section: Cdc Reactions Catalyzed By Coppermentioning

confidence: 99%

Recent Developments in Transition Metal‐Catalyzed Cross‐Dehydrogenative Coupling Reactions of Ethers and Thioethers

Phillips

Pombeiro

2018

ChemCatChem

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dehydrogenative coupling of two CÀH bonds or a CÀH and an XÀH bond (X=N, O, P, S, etc.) has emerged as a powerful new synthetic methodology in the last 12 years. Using this approach, simple ethers, often utilized as solvents, and more complex ones, as well as thioethers, have become important alkylating agents, when reacted directly, under oxidative conditions in the presence of suitable reagents. This environmentally friendly, sustainable procedure, has been used to alkylate a wide range of substrates, from simple ketones and acids to alkyl benzenes, coumarins, indoles, oxazoles, benzoxazoles or (benzo)thiazoles and more. This Review is a systematic presentation of the developments in transition metal-catalyzed CDC reactions, including photoredox processes, which took place between 2014 and early 2018, with an emphasis on the later years.

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Copper-Mediated Oxidative Functionalization of C(sp³)–H Bonds with Isoquinolines: Two-Step Synthesis of 5-Oxaprotoberberinones

Cited by 20 publications

References 39 publications

Cross-dehydrogenative coupling and oxidative-amination reactions of ethers and alcohols with aromatics and heteroaromatics

Cross-dehydrogenative coupling and oxidative-amination reactions of ethers and alcohols with aromatics and heteroaromatics

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Recent Developments in Transition Metal‐Catalyzed Cross‐Dehydrogenative Coupling Reactions of Ethers and Thioethers

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Copper-Mediated Oxidative Functionalization of C(sp3)–H Bonds with Isoquinolines: Two-Step Synthesis of 5-Oxaprotoberberinones

Cited by 20 publications

References 39 publications

Cross-dehydrogenative coupling and oxidative-amination reactions of ethers and alcohols with aromatics and heteroaromatics

Cross-dehydrogenative coupling and oxidative-amination reactions of ethers and alcohols with aromatics and heteroaromatics

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Recent Developments in Transition Metal‐Catalyzed Cross‐Dehydrogenative Coupling Reactions of Ethers and Thioethers

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Copper-Mediated Oxidative Functionalization of C(sp³)–H Bonds with Isoquinolines: Two-Step Synthesis of 5-Oxaprotoberberinones