NiCl2-catalyzed radical cross decarboxylative coupling between arylpropiolic acids and cyclic ethers

Wan, Zijuan; Wang, Jin‐Yuan; Luo, Jun

doi:10.1016/j.tetlet.2019.01.039

Cited by 8 publications

(1 citation statement)

References 62 publications

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“…Luo et al established a radical cross-decarboxylative coupling procedure catalysed by NiCl 2 and employing di-tert-butyl peroxide (DTBP) as the radical initiator and oxidant for the direct alkenylation of cyclic ethers. [27] They reacted a series of cyclic ethers 6 and arylpropiolic acids 5 under NiCl 2 (10 mol %), DTBP (1.2 equiv.) and K 2 CO 3 (1.1 equiv.)…”

Section: Ni-catalysed Couplingmentioning

confidence: 99%

Nickel‐Catalysed Decarboxylative Coupling Reactions – An Overview

Arunkumar,

Pallavi,

Philip

et al. 2024

ChemistrySelect

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Decarboxylative cross‐coupling is a significant method in organic synthesis where inexpensive and stable carboxylic acids are used as substrates for the construction of C−C and C‐heteroatom bonds. First‐row 3d transition metals including nickel have recently been recognized as advantageous alternative to noble metals in transition metal catalysed decarboxylative couplings. In this review, Ni‐based catalysts for C−C (Csp3/Csp2/Csp) and C‐heteroatom (C−N, C−P, C−S, C−Si) cross‐couplings are summarized and most of the strategies find applications in the synthesis and modification of biologically important molecules. Importantly, Ni‐dual catalysis under photocatalytic and electrochemical conditions form the state of the art research in the field. This is the first review reported exclusively on Ni‐catalysed decarboxylative cross‐coupling and cover reports from 2009 to present.

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Section: Ni-catalysed Couplingmentioning

confidence: 99%

Nickel‐Catalysed Decarboxylative Coupling Reactions – An Overview

Arunkumar,

Pallavi,

Philip

et al. 2024

ChemistrySelect

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Visible Light‐Catalyzed Decarboxylative Alkynylation of Arenediazonium Salts with Alkynyl Carboxylic Acids: Direct Access to Aryl Alkynes by Organic Photoredox Catalysis

Yang

et al. 2019

Adv Synth Catal

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A convenient method mediated by photoredox catalysis is developed for the direct construction of aryl alkynes. Readily available aromatic diazonium salts have been utilized as the aryl radical source to couple alkynyl carboxylic acids to feature the decarboxylative arylation. A wide range of substrates are amenable to this protocol with broad functional group tolerance, and diversely-functionalized aryl alkynes could be synthesized under mild, neutral and transition metal-free reaction conditions using visible light irradiation. Alongside synthetic sustainability associated with the photocatalytic and transition metal-free operation, another key point of this method is that the organic dye catalyst acts as an excited-state reductant, thus establishing the quenching cycle for radical addition and decarboxylative elimination.

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H₂O₂‐Promoted Alkoxyalkylation of Terminal Alkynes Employing Two Strategies with Transition‐Metal‐Free Conditions

Zhao

Hua²,

Wang

et al. 2022

Asian J Org Chem

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H 2 O 2 -promoted alkoxyalkylation of terminal alkynes by employing two strategies were developed, this is the first example of the direct C(sp 3 )À H functionalization of ethers to prepare 2-vinyl heterocycles by using H 2 O 2 as the radical initiator and oxidant. Particularly, this transformation could be conducted without expensive photocatalysts or transition metal catalysts under mild conditions.

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NiCl2-catalyzed radical cross decarboxylative coupling between arylpropiolic acids and cyclic ethers

Cited by 8 publications

References 62 publications

Nickel‐Catalysed Decarboxylative Coupling Reactions – An Overview

Nickel‐Catalysed Decarboxylative Coupling Reactions – An Overview

Visible Light‐Catalyzed Decarboxylative Alkynylation of Arenediazonium Salts with Alkynyl Carboxylic Acids: Direct Access to Aryl Alkynes by Organic Photoredox Catalysis

H₂O₂‐Promoted Alkoxyalkylation of Terminal Alkynes Employing Two Strategies with Transition‐Metal‐Free Conditions

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NiCl2-catalyzed radical cross decarboxylative coupling between arylpropiolic acids and cyclic ethers

Cited by 8 publications

References 62 publications

Nickel‐Catalysed Decarboxylative Coupling Reactions – An Overview

Nickel‐Catalysed Decarboxylative Coupling Reactions – An Overview

Visible Light‐Catalyzed Decarboxylative Alkynylation of Arenediazonium Salts with Alkynyl Carboxylic Acids: Direct Access to Aryl Alkynes by Organic Photoredox Catalysis

H2O2‐Promoted Alkoxyalkylation of Terminal Alkynes Employing Two Strategies with Transition‐Metal‐Free Conditions

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H₂O₂‐Promoted Alkoxyalkylation of Terminal Alkynes Employing Two Strategies with Transition‐Metal‐Free Conditions