The oxidation of acetophenones to arylglyoxals with aqueous hydrobromic acid in dimethyl sulfoxide

Floyd, M. Brawner; Du, Mengcheng; Fabio, P. F.; Jacob, Linda; Johnson, Bernard

doi:10.1021/jo00225a004

Cited by 122 publications

(62 citation statements)

References 4 publications

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“…It oxidizes HBr to electrophilic Br 2 , which undergoes a nucleophilic displacement reaction with DMSO to generate the bromodimethylsulfoxonium ion (Scheme ). Some of the well‐known reactions executed by this intermediate include the bromination of electron‐rich aromatic systems, dibromination of alkenes, oxidation of phenylacetylene to benzil, and oxidation of acetophenone to phenylglyoxal (Scheme ) …”

Section: Lewis‐base‐coordinated Halogen(i) Intermediates Generatedmentioning

confidence: 99%

Role of Lewis‐Base‐Coordinated Halogen(I) Intermediates in Organic Synthesis: The Journey from Unstable Intermediates to Versatile Reagents

et al. 2017

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The widespread use of halogen‐based reagents in organic synthesis is well known. Hypervalent halogens (oxidation states III and V) have been explored to a significant extent. Among them, hypervalent iodine reagents have found major use and applications. In contrast, understanding of the reactivity of halogen(I) species in the presence of Lewis bases, and their reaction mechanisms, are very limited. This microreview sheds light on the importance of halogen(I) species and their applications in organic synthesis. In commercially available halogen(I) precursors such as N‐halosuccinimides, the halogen atom is attached to the nitrogen atom through a covalent bond with low electrophilicity and thus low reactivity. Interestingly, the reactivity increases if the electrophilic halogen(I) atom is attached to a Lewis base through a polarized covalent bond. The halogen‐bonding interaction between the Lewis base and the halonium ion (or halonium ion equivalent) results in highly reactive and thermodynamically stable halogen(I) intermediates that act as versatile reagents. This microreview unravels the evolution of the unstable halogen(I) intermediates to become versatile reagents.

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Section: Lewis‐base‐coordinated Halogen(i) Intermediates Generatedmentioning

confidence: 99%

Role of Lewis‐Base‐Coordinated Halogen(I) Intermediates in Organic Synthesis: The Journey from Unstable Intermediates to Versatile Reagents

et al. 2017

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“…18 with the last step following the modified procedure by Floyd et al . 19 . The starting tertiary amine 1 was prepared in ten steps from commercially available 3-bromo-2-methylbenzoic acid via an Arndt-Eistert homologation to 2-(3-bromo-2-methylphenyl)acetate 20 , followed by a double Grignard addition to the ester and a Ritter reaction of the resulting tertiary alcohol 21 .…”

Section: Resultsmentioning

confidence: 99%

High-Affinity Functional Fluorescent Ligands for Human β-Adrenoceptors

Mitronova

Lukinavičius

Butkevich

et al. 2017

Sci Rep

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Visualization of the G-protein coupled receptor (GPCR) is of great importance for studying its function in a native cell. We have synthesized a series of red-emitting fluorescent probes targeting β-adrenergic receptor (βAR) that are compatible with confocal and Stimulated Emission Depletion (STED) microscopy as well as with Time-Resolved Fluorescence Resonance Energy Transfer (TR-FRET) binding assay in living cells. The probe based on the agonist BI-167107 and fluorescent dye KK114 demonstrates nanomolar binding affinity and up to nine-fold β2AR selectivity over β1AR. Carazolol-derived probes are fluorogenic and allow no-wash imaging experiments. STED microscopy of β2ARs stained at the native expression level on pancreatic CAPAN cells provides two-fold improvement in lateral optical resolution over confocal mode and reveals the formation of receptor microdomains. These probes retain their functional (agonist or antagonist) properties, allowing simultaneous modulation of cyclic adenosine monophosphate (cAMP) levels and receptor internalization as well as imaging receptor localization.

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“…( E )‐1,4‐Bis(4‐nitrophenyl)but‐2‐ene‐1,4‐dione (2e): The title compound was prepared by a two‐step procedure. In the first step, p ‐nitroacetophenone was transformed into p ‐nitro‐α‐oxo‐benzeneacetaldehyde by using a reported procedure 17. In the second step, p ‐nitro‐α‐oxo‐benzeneacetaldehyde (375 mg; 2.09 mmol) was dissolved in anhydrous CH 2 Cl 2 (10 mL), and a solution of 1‐ p ‐nitrophenyl‐2‐triphenylphosphoranylidene‐ethanone (1.2 g; 2.8 mmol/10 mL) in CH 2 Cl 2 was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

Asymmetric Diastereoselective Synthesis of Spirocyclopropane Derivatives of Oxindole

Ošeka¹,

Noole²,

Žari³

et al. 2014

Eur J Org Chem

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The oxidation of acetophenones to arylglyoxals with aqueous hydrobromic acid in dimethyl sulfoxide

Cited by 122 publications

References 4 publications

Role of Lewis‐Base‐Coordinated Halogen(I) Intermediates in Organic Synthesis: The Journey from Unstable Intermediates to Versatile Reagents

Role of Lewis‐Base‐Coordinated Halogen(I) Intermediates in Organic Synthesis: The Journey from Unstable Intermediates to Versatile Reagents

High-Affinity Functional Fluorescent Ligands for Human β-Adrenoceptors

Asymmetric Diastereoselective Synthesis of Spirocyclopropane Derivatives of Oxindole

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