Organolead‐Mediated Arylations: 2‐(3,3‐Diphenylallyloxy)phenyllead Triacetate as an Internal Free‐Radical‐Trap‐Containing Reagent

Fedorov, Alexey Yu.; Finet, Jean‐Pierre

doi:10.1002/ejoc.200300784

Cited by 15 publications

(6 citation statements)

References 44 publications

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“…The selective reaction with styrene is also seen when it is used in place of trans-stilbene. A radical intermediate would be expected to react preferentially with 1,1-diphenylethene [28] so it is unlikely that radical intermediate 34 is involved in the aziridination reaction.…”

Section: Resultsmentioning

confidence: 99%

Hypervalent Iodine‐Mediated Aziridination of Alkenes: Mechanistic Insights and Requirements for Catalysis

Desaize¹,

Wirth²

2007

Chemistry A European J

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By detailed study of the possible side reactions in the previously reported aziridination of alkenes with N-aminoheterocycles mediated by hypervalent iodine reagents, the requirements to make this reaction catalytic in iodoarene have been determined. The reaction requires an oxidant that will oxidise iodoarenes but that does not oxidise alkenes, but it is possible that no such oxidant actually exists! A method in which the hypervalent iodine reagent can be recycled without the need for reisolation is possible. Further study into the mechanism of this reaction gives tentative evidence that the reaction proceeds through formation of an aminoiodane that reacts directly with the alkene, contrary to previous literature reports in which an acetoxyamine intermediate is suggested. The temperature effect of this reaction is remarkable.

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Section: Resultsmentioning

confidence: 99%

Hypervalent Iodine‐Mediated Aziridination of Alkenes: Mechanistic Insights and Requirements for Catalysis

Desaize¹,

Wirth²

2007

Chemistry A European J

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“…67,72 For example, the lack of inhibition by radical scavengers or oxygen (compare with Bethell's results above) in the reaction mixture, made the authors think that this coupling did not occur through radical aromatic substitution. 67,72 Radical clock experiments (Scheme 13) have been performed many times on thermal reactions 67,[73][74][75][76][77][78][79] to investigate the existence of aryl radical intermediates in the reaction medium, and negative results have been obtained so far. A small amount of radicalderived product was detected only once from these experiments, showing that radical mechanisms can actually occur in the reaction, although to a minimal extent.…”

Section: Mechanismsmentioning

confidence: 99%

Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development

et al. 2014

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Cu-catalysed arylation reactions devoted to the formation of C-C and C-heteroatom bonds (Ullmann-type couplings) have acquired great importance in the last decade. This review discusses the history and development of coupling reactions between aryl halides and various classes of nucleophiles, focusing mostly on the different mechanisms proposed through the years. Selected mechanistic investigations are treated more in depth than others. For example, evidence in favour or against radical mechanisms is discussed. Cu(I) and Cu(III) complexes involved in the Ullmann reaction and N/O selectivity in aminoalcohol arylation are discussed. A separate section has been dedicated to the synthesis of heterocyclic rings through intramolecular couplings. Finally, recent developments in green chemistry for these reactions, such as reactions in aqueous media and heterogeneous catalysis, have also been reviewed.

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“…This step involves a reductive ligand coupling 28 C-arylation reaction, which has been realized by using aryl derivatives of lead, 17,18 bismuth, 17,29 iodine, 17,30 and some other heteroatoms. 17 Supposedly, this process involves the formation of the covalent intermediate 9, 18,31 which under-…”

Section: Figurementioning

confidence: 99%

2-(Azidomethyl)arylboronic Acids in the Synthesis of Coumarin-Type Compounds

Naumov¹,

Nuchev²,

Sitnikov³

et al. 2009

Synthesis

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Several 2-(azidomethyl)arylboronic acids were synthesized. Their involvement into organolead-mediated Pinhey arylation reaction with 4-hydroxycoumarins afforded 3-[2-(azidomethyl)aryl]-4-hydroxycoumarins or [4,3-c]isoquinolinocoumarins in reasonable yields via two-or four-step one-pot reaction sequence. Palladium-catalyzed cross-coupling of organoboron reagents with 4-trifluoromethylsulfonyloxycoumarins under Suzuki reaction conditions gave 4-[2-(azidomethyl)aryl]coumarins in good yields. 2-(Azidomethyl)arylboronic acid, as well as azide-containing iso-and neoflavonoid compounds underwent catalytic alkyneazide cycloaddition in THF-water, providing 1,4-triazole compounds regioselectively in good to excellent yields.

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Organolead‐Mediated Arylations: 2‐(3,3‐Diphenylallyloxy)phenyllead Triacetate as an Internal Free‐Radical‐Trap‐Containing Reagent

Cited by 15 publications

References 44 publications

Hypervalent Iodine‐Mediated Aziridination of Alkenes: Mechanistic Insights and Requirements for Catalysis

Hypervalent Iodine‐Mediated Aziridination of Alkenes: Mechanistic Insights and Requirements for Catalysis

Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development

2-(Azidomethyl)arylboronic Acids in the Synthesis of Coumarin-Type Compounds

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