Über die Einwirkung aromatischer Diazoverbindungen auf α,β‐ungesättigte Carbonylverbindungen

Meerwein, Hans; Büchner, Eberhard; Emster, Konrad van

doi:10.1002/prac.19391520705

Cited by 280 publications

(136 citation statements)

References 8 publications

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“…This article will give an overview over recent advances and developments in the field of intermolecular Meerwein type arylation reactions. [28,29] Meerwein arylations represent the synthetically most valuable transformations based on aryl radicals. The structural variability of each of the three reactants involved in the process, that is, the aryl radical source, the olefin and the trapping reagent, leads to a broad scope of this radical multicomponent reaction.…”

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confidence: 99%

Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts

Heinrich

2009

Chemistry A European J

283

104

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This minireview is aimed at giving an overview of recent advances in olefin functionalisation reactions involving aryl radicals generated from arenediazonium salts. Based on the well-known Meerwein arylation, in which an aryl and a halogen substituent are coupled to an olefinic substrate, new reaction types have been developed that allow the introduction of a broad spectrum of other atoms and functional groups at the place of the original halogen atom and that are applicable to an extended range of olefinic substrates.

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confidence: 99%

Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts

Heinrich

2009

Chemistry A European J

283

104

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“…[1] The classic Meerwein arylation has two alternative reaction pathways: a) Meerwein arylation-elimination, in which aryl-alkene cross-coupling products are formed exclusively, and b) Meerwein arylationaddition, in which the aryl radical and a halogen atom add to an olefinic substrate. [1b] The addition of atoms other than halogen has also been reported.…”

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confidence: 99%

The Photoredox‐Catalyzed Meerwein Addition Reaction: Intermolecular Amino‐Arylation of Alkenes

2013

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A variety of amides are efficiently accessible under mild conditions by intermolecular amino-arylation using a photo Meerwein addition with visible light. The reaction has a broad substrate scope, tolerates a large range of functional groups, and was applied to the synthesis of a 3-aryl-3,4-dihydroisoquinoline.The Meerwein arylation is a valuable synthetic transformation based on aryl radical chemistry. [1] The classic Meerwein arylation has two alternative reaction pathways: a) Meerwein arylation-elimination, in which aryl-alkene cross-coupling products are formed exclusively, and b) Meerwein arylationaddition, in which the aryl radical and a halogen atom add to an olefinic substrate. [1b] The addition of atoms other than halogen has also been reported. [1b] However, photo Meerwein arylations have been applied so far only for the formation of aryl-alkene coupling products and have not been extended to the valuable alkene addition products [2] obtainable under classical Meerwein arylation conditions. [3] The challenge in obtaining the addition product is the competing reaction of the trapping reagent or nucleophile with the diazonium salt leading to undesired products (Scheme 1). [1b] The Ritter-type amination reaction is a most useful transformation for the formation of CÀN bonds and has been used in industrial processes for the synthesis of the anti-HIV drug Crixivan, the alkaloid aristotelone, and amantadine. [2d, 4] We utilize the Ritter reaction conditions to trap the carbenium ion, which is generated during the photoredox Meerwein arylation, thus allowing the intermolecular aminoarylation of alkenes mediated by visible light.Our initial studies began with the attempted reaction of diazonium salt 1 a (0.25 mmol) with 5 equiv of styrene 2 a using 2 mol % of [Ru(bpy) 3 ]Cl 2 in 1.0 mL of CH 3 CN containing 10 equiv of water under visible-light irradiation for 4 h at 20 8C; the desired product 3 a was obtained in 42 % yield (Table 1, entry 1) along with 1,2-diphenylethanol as a byproduct. We examined the influence of the amount of water, the catalyst loading, and the number of equivalents of styrene on this multicomponent photoreaction. To our delight, the desired product 3 a was obtained in 88 % yield (Table 1, entry 6) when diazonium salt 1 a (0.25 mmol), 0.5 mol % of [Ru(bpy) 3 ]Cl 2 , 2 equiv of styrene 2 a, and 1 equiv of water were used in 1.0 mL of CH 3 CN. The reaction yields of 3 a are significantly affected by the amount of water: a larger amount

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“…The Meerwein reaction, [7] a copper-catalyzed redox transformation between diazonium ions and olefins, can be formally classified as a C À H arylation since the products are usually synthetically equivalent to those obtained through a Pd-catalyzed Heck reaction. However, the generally low efficiency of the Meerwein reaction precluded its development from further synthetic relevant applications.…”

Section: Arenediazonium Saltsmentioning

confidence: 99%

“…Although this approach has been known for a long time with the work of Meerwein, [7] it only recently turned out to be efficient with the development of novel catalytic systems. This review aims to provide a picture of the actual state-of-the-art involving the arylation of heteroarenes or by extension, olefin-containing heterocycles, with aryl radicals generated by transition metals.…”

Section: Introductionmentioning

confidence: 99%

Transition Metal‐Mediated Direct CH Arylation of Heteroarenes Involving Aryl Radicals

2014

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This review gives an overview of the generation of aryl radicals, mediated by transition metals, and their use for the C À H arylation of heteroarenes. The different sources of aromatic derivatives able to generate aryl radicals via a metal-assisted reduction or oxidation are discussed, with a critical view of the developed systems. The radical arylations of nitrogen-, oxygen-or sulfur-containing heterocycles are then described and mechanistic considerations are discussed as well.

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Über die Einwirkung aromatischer Diazoverbindungen auf α,β‐ungesättigte Carbonylverbindungen

Cited by 280 publications

References 8 publications

Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts

Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts

The Photoredox‐Catalyzed Meerwein Addition Reaction: Intermolecular Amino‐Arylation of Alkenes

Transition Metal‐Mediated Direct CH Arylation of Heteroarenes Involving Aryl Radicals

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