Nickelaelektro‐katalysierte C‐H‐Alkoxylierung mit sekundären Alkoholen: oxidationsinduzierte reduktive Eliminierung an Nickel(III)

Zhang, Shou‐Kun; Struwe, Julia; Hu, Lianrui; Ackermann, Lutz

doi:10.1002/ange.201913930

Cited by 20 publications

(2 citation statements)

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“…reported a nickel catalyzed C−H electro‐alkoxylation with sterically encumbered secondary alcohols (Scheme 53). [60] They examine the versatility of the nickela‐electrocatalyzed C−H alkoxylation with various secondary alcohols. They examine the versatility of the nickela‐electrocatalyzed C−H alkoxylation with various secondary alcohols.…”

Section: Electrochemically Driven Nickel‐catalyzed Reactionsmentioning

confidence: 99%

Review of electrochemical transition‐metal‐catalyzed C−H functionalization reactions

2023

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The combination of organometallic C−H activation and electro‐catalysis has emerged as a potent synthetic technique for various molecular scaffolds since it avoids the use of harmful and expensive chemical oxidants in stoichiometric amounts. Moreover, the pre‐functionalization of substrates is not required and newer ways to perform metal‐catalyzed C−H activation reactions are possible. Here, we have discussed eletrochemically driven C−H acyloxylation, acetoxylation, oxygenation, acylation, amination, alkylation, halogenation, olefinations and C−H/N−H annulation reactions using various transition‐metal‐catalyst such as Ru, Rh, Pd, Co, Ni, Ir, Cu, Mn and Au by anodic oxidation, followed by reductive elimination to form the corresponding C−O, C−C, C−N and C−X (X=Cl, Br, S etc.) bonds. This review covers recent developments in transition‐metal‐catalyzed electrochemical C−H activation from 2007 until 2022.

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Section: Electrochemically Driven Nickel‐catalyzed Reactionsmentioning

confidence: 99%

Review of electrochemical transition‐metal‐catalyzed C−H functionalization reactions

2023

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“…It is probably due to that the increased electron-density at the quinolinyl nitrogen enhanced the coordination to metal center, which would facilitate CÀ F bond oxidative addition. [24] In sharp contrast, no desired carboxylation product was obtained in the reaction of monodentate amide.…”

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confidence: 99%

Nickel‐Catalyzed Carboxylation of Aryl C−F Bonds with CO₂

Pei

Wang

2022

Adv Synth Catal

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The C−F bond is the strongest single bond and it is one of the most challenging tasks to achieve the C−F bond functionalization. Here, we describe the first nickel‐catalyzed selective defluorinative carboxylation of aryl C−F bonds with CO2. Various methyl carboxylates including partially fluorinated carboxylation compounds were obtained. Mechanistic studies reveal that the azanickelacycles might be vital intermediates in this transformation. This novel and straightforward carboxylation strategy will extend the scope of C−F bond functionalization and enhance the understanding of the reactivity of very stable bonds.

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Ni‐Catalyzed Direct Carboxylation of Aryl C−H Bonds in Benzamides with CO₂

Pei

Zong

et al. 2021

Adv Synth Catal

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The direct carboxylation of inert aryl C−H bond catalyzed by abundant and cheap nickel is still facing challenge. Herein, we report the Ni‐catalyzed direct carboxylation of aryl C−H bonds in benzamides under 1 atm of CO2 to afford various methyl carboxylates or phthalimides, dealing with different post‐processing. The reaction displays excellent functional group tolerance and affords moderate to high carboxylation yields under mild conditions. Detail mechanistic studies suggest that a Ni(0)−Ni(II)−Ni(I) catalytic cycle may be involved in this reaction.

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Nickelaelektro‐katalysierte C‐H‐Alkoxylierung mit sekundären Alkoholen: oxidationsinduzierte reduktive Eliminierung an Nickel(III)

Cited by 20 publications

References 149 publications

Review of electrochemical transition‐metal‐catalyzed C−H functionalization reactions

Review of electrochemical transition‐metal‐catalyzed C−H functionalization reactions

Nickel‐Catalyzed Carboxylation of Aryl C−F Bonds with CO₂

Ni‐Catalyzed Direct Carboxylation of Aryl C−H Bonds in Benzamides with CO₂

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Nickelaelektro‐katalysierte C‐H‐Alkoxylierung mit sekundären Alkoholen: oxidationsinduzierte reduktive Eliminierung an Nickel(III)

Cited by 20 publications

References 149 publications

Review of electrochemical transition‐metal‐catalyzed C−H functionalization reactions

Review of electrochemical transition‐metal‐catalyzed C−H functionalization reactions

Nickel‐Catalyzed Carboxylation of Aryl C−F Bonds with CO2

Ni‐Catalyzed Direct Carboxylation of Aryl C−H Bonds in Benzamides with CO2

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Product

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About

Nickel‐Catalyzed Carboxylation of Aryl C−F Bonds with CO₂

Ni‐Catalyzed Direct Carboxylation of Aryl C−H Bonds in Benzamides with CO₂