Direct ni mediated synthesis of ketones from acyl bromides and grignard reagents

Malanga, C.; Aronica, Laura Antonella; Lardicci, L.

doi:10.1016/0040-4039(95)01936-c

Cited by 40 publications

(13 citation statements)

References 16 publications

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“…To the best of our knowledge, there is only one publication claiming the use of dithianes in a catalytic reaction as acyl anion equivalents 8. This manuscript involves the nickel‐catalyzed reaction of preformed 2‐lithio‐1,3‐dithianes with benzoyl halides to form 1,2‐diketones derivatives (average yield 46 %) 9. The conflicting description in this manuscript makes it unclear if benzoyl chlorides or bromides were actually employed.…”

Section: Introductionmentioning

confidence: 99%

Liposomal Encapsulation of a Near‐Infrared Fluorophore Enhances Fluorescence Quenching and Reliable Whole Body Optical Imaging Upon Activation In Vivo

Tansi

Rüger

Rabenhold

et al. 2013

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In the past decade, there has been significant progress in the development of water soluble near-infrared fluorochromes for use in a wide range of imaging applications. Fluorochromes with high photo and thermal stability, sensitivity, adequate pharmacological properties and absorption/emission maxima within the near infrared window (650-900 nm) are highly desired for in vivo imaging, since biological tissues show very low absorption and auto-fluorescence at this spectrum window. Taking these properties into consideration, a myriad of promising near infrared fluorescent probes has been developed recently. However, a hallmark of most of these probes is a rapid clearance in vivo, which hampers their application. It is hypothesized that encapsulation of the near infrared fluorescent dye DY-676-COOH, which undergoes fluorescence quenching at high concentrations, in the aqueous interior of liposomes will result in protection and fluorescence quenching, which upon degradation by phagocytes in vivo will lead to fluorescence activation and enable imaging of inflammation. Liposomes prepared with high concentrations of DY-676-COOH reveal strong fluorescence quenching. It is demonstrated that the non-targeted PEGylated fluorescence-activatable liposomes are taken up predominantly by phagocytosis and degraded in lysosomes. Furthermore, in zymosan-induced edema models in mice, the liposomes are taken up by monocytes and macrophages which migrate to the sites of inflammation. Opposed to free DY-676-COOH, prolonged stability and retention of liposomal-DY-676-COOH is reflected in a significant increase in fluorescence intensity of edema. Thus, protected delivery and fluorescence quenching make the DY-676-COOH-loaded liposomes a highly promising contrast agent for in vivo optical imaging of inflammatory diseases.

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Section: Introductionmentioning

confidence: 99%

Liposomal Encapsulation of a Near‐Infrared Fluorophore Enhances Fluorescence Quenching and Reliable Whole Body Optical Imaging Upon Activation In Vivo

Tansi

Rüger

Rabenhold

et al. 2013

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“…Functionalized aryl-and heteroaryl-magnesium reagents have become readily available from the corresponding organic iodides or bromides through a halogen-magnesium exchange by the reaction with the mixed complex iPrMgCl·LiCl [2] or by deprotonation of aryls and heteroaryls with LiCl-solubilized magnesium amides. [3] Typical procedures for the preparation of the unsymmetrical diaryl ketones starting from arylmagnesium reagents involve the use of transition metals, such as Cu I , [4] Fe III , [5] Ni II , [6] and Pd II , [7] or expensive ligands [8] followed by the addition of corresponding acyl chlorides.…”

Section: Introductionmentioning

confidence: 99%

The Mg‐Oppenauer Oxidation as a Mild Method for the Synthesis of Aryl and Metallocenyl Ketones

Kloetzing

Krasovskiy

Knöchel

2006

Chemistry A European J

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Magnesium alkoxides undergo a hydride‐transfer oxidation with benzaldehyde as the oxidant. This magnesium variant of the Oppenauer oxidation was used for the synthesis of polyfunctional biaryl ketones. LiCl was found to promote this reaction by enhancing the solubility of magnesium alkoxides. This mild oxidation method was especially useful for preparing ketones bearing a metallocenyl unit as well as various new ferrocenyl ketones and tricarbonylchromium complexes. This last class of ketones was reduced with the CBS catalyst (CBS=Corey–Bakshi–Shibata, diphenyl oxazaborolidine) to chiral benzhydrol complexes with high enantioselectivity enabling an asymmetric synthesis of electron‐rich or ‐poor benzhydryl alcohols (up to 94 % ee).

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“…3-Phenyl-1-(thiophen-2-yl)butanone ( 3m ) [ 48 ]: Colorless oil (111.5 mg, 97%). 1 H-NMR (400 MHz, CDCl 3 ) δ(ppm): 7.70–7.69 (m, 1H, thiophenyl), 7.64–7.63 (m, 1H, thiophenyl), 7.36–7.28 (m, 4H, Ph), 7.25–7.23 (m, 1H, Ph), 7.14–7.12 (m, 1H, thiophenyl), 3.56–3.51 (m, 1H, PhCH), 3.24 (dd, J 1 = 16.0 Hz, J 2 = 6.0 Hz, 1H, CH 2 CO), 3.14 (dd, J 1 = 15.6 Hz, J 2 = 8.4 Hz, 1H, CH 2 CO), 1.38 (d, J = 6.8 Hz, 3H, CH 3 ).…”

Section: Methodsmentioning

confidence: 99%

Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes

Shi

Zou

2018

Molecules

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A highly efficient acylative cross-coupling of trialkylboranes with activated amides has been effected at room temperature to give the corresponding alkyl ketones in good to excellent yields by using 1,3-bis(2,6-diisopropyl)phenylimidazolylidene and 3-chloropyridine co-supported palladium chloride, the PEPPSI catalyst, in the presence of K2CO3 in methyl tert-butyl ether. The scope and limitations of the protocol were investigated, showing good tolerance of acyl, cyano, and ester functional groups in the amide counterpart while halo group competed via the classical Suzuki coupling. The trialkylboranes generated in situ by hydroboration of olefins with BH3 or 9-BBN performed similarly to those separately prepared, making this protocol more practical.

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Direct ni mediated synthesis of ketones from acyl bromides and grignard reagents

Cited by 40 publications

References 16 publications

Liposomal Encapsulation of a Near‐Infrared Fluorophore Enhances Fluorescence Quenching and Reliable Whole Body Optical Imaging Upon Activation In Vivo

Liposomal Encapsulation of a Near‐Infrared Fluorophore Enhances Fluorescence Quenching and Reliable Whole Body Optical Imaging Upon Activation In Vivo

The Mg‐Oppenauer Oxidation as a Mild Method for the Synthesis of Aryl and Metallocenyl Ketones

Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes

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