Application of copper(<scp>i</scp>) salt and fluoride promoted Stille coupling reactions in the synthesis of bioactive molecules

Lee, Victor

doi:10.1039/c9ob01602c

Cited by 33 publications

(21 citation statements)

References 84 publications

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“…On the first step, the crude reaction mixture obtained was added to an aqueous solution of potassium fluoride (KF) according to a reported literature procedure using an alcoholic KF solution [51]. The KF solution was allowed to react with the tin by-product in the mixture, so that the tin by-product precipitates into a white powder of polymeric Bu 3 SnF [2] and is removed by filtration. This was repeated until no residue was observed in the flask.…”

Section: Purification Of Crude Product Mixture From Pd-catalyzed Stilmentioning

confidence: 99%

“…Most importantly, the Stille, Suzuki-Miyaura, Heck, Negishi and Sonogashira coupling reactions typically catalyzed by palladium have been abundantly used in syntheses and widely studied in recent decades. Stille coupling, which is the palladium-catalyzed cross-coupling of an organostannane and an organohalide, is one of the most powerful methods for the straightforward joining together of carbon-carbon bonds in synthetic chemistry [1][2][3]. It is currently a widely used cross-coupling method for the synthesis of functional molecules and polymers, both in laboratory research and in industry [1,4].…”

Section: Introductionmentioning

confidence: 99%

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Recoverable Palladium-Catalyzed Carbon-Carbon Bond Forming Reactions under Thermomorphic Mode: Stille and Suzuki-Miyaura Reactions

et al. 2021

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The reaction of [PdCl2(CH3CN)2] and bis-4,4’-(RfCH2OCH2)-2,2’-bpy (1a–d), where Rf = n-C11F23 (a), n-C10F21 (b), n-C9F19 (c) and n-C8F17 (d), respectively, in the presence of dichloromethane (CH2Cl2) resulted in the synthesis of Pd complex, [PdCl2[4,4’-bis-(RfCH2OCH2)-2,2’-bpy] (2a–d). The Pd-catalyzed Stille arylations of vinyl tributyltin with aryl halides were selected to demonstrate the feasibility of recycling usage with 2a as the catalyst using NMP (N-methyl-2-pyrrolidone) as the solvent at 120–150 °C. Additionally, recycling and electronic effect studies of 2a–c were also carried out for Suzuki-Miyaura reaction of phenylboronic acid derivatives, 4-X-C6H4-B(OH)2, (X = H or Ph) with aryl halide, 4-Y-C6H4-Z, (Y = CN, H or OCH3; Z = I or Br) in dimethylformamide (DMF) at 135–150 °C. At the end of each cycle, the product mixtures were cooled to lower temperature (e.g., −10 °C), and then catalysts were recovered by decantation with Pd leaching less than 1%. The products were quantified by gas chromatography/mass spectrometry (GC/MS) analysis or by the isolated yield. The complex 2a-catalyzed Stille reaction of aryl iodides with vinyl tributyltin have good recycling results for a total of 8 times, with a high yield within short period of time (1–3 h). Similarly, 2a–c-catalyzed Suzuki-Miyaura reactions also have good recycling results. The electronic effect studies from substituents in both Stille and Suzuki-Miyaura coupling reactions showed that electron withdrawing groups speed up the reaction rate. To our knowledge, this is the first example of recoverable fluorous long-chained Pd-catalyzed Stille reactions under the thermomorphic mode.

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Section: Purification Of Crude Product Mixture From Pd-catalyzed Stilmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recoverable Palladium-Catalyzed Carbon-Carbon Bond Forming Reactions under Thermomorphic Mode: Stille and Suzuki-Miyaura Reactions

et al. 2021

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“…Copper iodide (CuI) has a wide application in nonlinear optics [1,2], solar cells development [3], photocatalysis [4], photoluminescention [5], electrophysics [6,7] and conventional analytical chemistry, i.e., mercury detection [8]. Apart from those, CuI is used as a perspective catalyst in a large number of organic synthesis, viz., Heck-types reactions [9,10], Stills-types [11], Ullmann-type routes [12][13][14][15][16][17][18][19] Suzuki-Miyaura and Sonogashira reactions of cross-coupling [20][21][22] and many others [19,[22][23][24][25][26][27]. In addition, CuI was reported as an effective electrocatalyst in hydrazine-related synthesis [28] and formic acid oxidation [29].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Copper Iodide-Polypyrrole Nanocomposites

et al. 2021

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A novel one-pot chemical synthesis of functional copper iodide-polypyrrole composites, CuI-PPy, has been proposed. The fabrication process allows the formation of nanodimensional metal salt/polymer hybrid structures in a fully controlled time- and concentration-dependent manner. The impact of certain experimental conditions, viz., duration of synthesis, sequence of component addition and concentrations of the intact reagents on the structure, dimensionality and yield of the end-product was evaluated in detail. More specifically, the amount of marshite CuI within the hybrid composite can be ranged from 60 to 90 wt.%, depending on synthetic conditions (type and concentration of components, process duration). In addition, the conditions allowing the synthesis of nano-sized CuI distributed inside the polypyrrole matrix were found. A high morphological stability and reproducibility of the synthesized nanodimensional metal-polymer hybrid materials were approved. Finally, the electrochemical activity of the formed composites was verified by cyclic voltammetry studies. The stability of CuI-PPy composite deposited on the electrodes was strongly affected by the applied anodic limit. The proposed one-pot synthesis of the hybrid nanodimensional copper iodide-polypyrrole composites is highly innovative, meets the requirements of Green Chemistry and is potentially useful for future biosensor development. In addition, this study is expected to generally contribute to the knowledge on the hybrid nano-based composites with tailored properties.

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“…An earlier report on the total synthesis of oxazolomycins provides an overview of the author's synthetic efforts toward neooxazolomycin (4), oxazolomycin A (5a), and related antibiotics [17]. The recent review of Lee has mainly focused on the application of copper(I) salt and fluoridepromoted Stille coupling reactions in the synthesis of bioactive molecules including inthomycins A-C (1-3) [18]. The present review provides a systematic summary of synthetic strategies for the synthesis of inthomycins and their analogues over the period of 1999 to present.…”

Section: Introductionmentioning

confidence: 99%

Progress in the total synthesis of inthomycins

Senapati¹

2021

Beilstein J. Org. Chem.

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The inthomycin family of antibiotics, isolated from Streptomyces strains, are interesting molecules for synthesis due to their characteristic common oxazole polyene chiral allylic β-hydroxycarbonyl fragments and significant biological activities. The full structural motif of the inthomycins is found in several more complex natural products including the oxazolomycins, 16-methyloxazolomycin, curromycins A and B, and KSM-2690. This review summarises the application of various efforts towards the synthesis of inthomycins and their analogues systematically.

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Application of copper(i) salt and fluoride promoted Stille coupling reactions in the synthesis of bioactive molecules

Abstract: This review summarises the synthesis of bioactive molecules through the use of Cu(i) salt and fluoride promoted Stille coupling reactions.

Cited by 33 publications

References 84 publications

Recoverable Palladium-Catalyzed Carbon-Carbon Bond Forming Reactions under Thermomorphic Mode: Stille and Suzuki-Miyaura Reactions

Recoverable Palladium-Catalyzed Carbon-Carbon Bond Forming Reactions under Thermomorphic Mode: Stille and Suzuki-Miyaura Reactions

One-Pot Synthesis of Copper Iodide-Polypyrrole Nanocomposites

Progress in the total synthesis of inthomycins

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