Utilizing a copper-free Sonogashira reaction in the synthesis of the leukotriene a4 hydrolase modulator batatasin IV

Petruncio, Greg; Girgis, Michael; Moummi, Sanae; Jayatilake, Meth; Lee, Kyung Hyeon; Paige, Mikell

doi:10.1016/j.tetlet.2020.152547

Cited by 4 publications

(9 citation statements)

References 17 publications

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“…Purification of the products was carried out by column chromatography using slica gel (mesh size 200−300) which was acquired from Qingdao Ocean Chemical. 1 H, 13 C, and 19 F NMR spectra were recorded with JEOL JNM-ECZS 400 MHz spectrometers. Chemical shifts (δ values) were reported in parts per million (ppm), with coupling constants in Hz.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…4-(4-Aminophenyl)-2-methylbut-3-yn-2-ol (1a). 19 According to reported literature, 20 4-iodoaniline (7.0 g, 31.95 mmol) was dissolved in TEA (25 mL); then, 2-methylbut-3-yn-2-ol (4.03 g, 5.9 mmol), copper(I) iodide (0.3 g, 1.6 mmol), and bis(triphenylphosphine) palladium chloride (0.45 g, 0.64 mmol) were added. The reaction mixture was stirred at room temperature for 3 h under nitrogen.…”

Section: Yield Calculation Examplementioning

confidence: 99%

“…1 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol (1f). 19 Following general procedure B, 1-iodo-4-nitrobenzene (1. 2-Methyl-4-(4-(trifluoromethyl)phenyl)but-3-yn-2-ol (1g).…”

Section: Yield Calculation Examplementioning

confidence: 99%

“…13 C{ 1 H} NMR (101 MHz, chloroform-d) δ 131.96, 130.07 (q, J = 32.9 Hz), 126.65, 123.97 (q, J = 273.54 Hz), 125.27 (q, J = 3.43 Hz), 96.24, 80.96, 65.71, 31.41. 19 F NMR (376 MHz, chloroform-d) δ −62.70.…”

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confidence: 99%

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Hydrazine Hydrate Accelerates Neocuproine–Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation

et al. 2021

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Diimine (HNNH) is a strong reducing agent, but the efficiency of diimine oxidized from hydrazine hydrate or its derivatives is still not good enough. Herein, we report an in situ neocuproine–copper complex formation method. The redox potential of this complex enable it can serve as an ideal redox catalyst in the synthesis of diimine by oxidation of hydrazine hydrate, and we successfully applied this technique in the reduction of alkynes. This reduction method displays a broad functional group tolerance and substrate adaptability as well as the advantages of safety and high efficiency. Especially, nitro, benzyl, boc, and sulfur containing alkynes can be reduced to the corresponding alkanes directly, which provides a useful complementary method to traditional catalytic hydrogenation. Besides, we applied this method in the preparation of the Alzheimer’s disease drug CT-1812 and studied the mechanism.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Yield Calculation Examplementioning

confidence: 99%

“…1 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol (1f). 19 Following general procedure B, 1-iodo-4-nitrobenzene (1. 2-Methyl-4-(4-(trifluoromethyl)phenyl)but-3-yn-2-ol (1g).…”

Section: Yield Calculation Examplementioning

confidence: 99%

mentioning

confidence: 99%

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Hydrazine Hydrate Accelerates Neocuproine–Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation

et al. 2021

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“…To further demonstrate the usefulness of this direct C–H arylation reaction of brominated arenes, we conducted the transformation of the C–Br bond to other functional groups (Scheme ). The coupling product 4f was prepared by direct arylation of 3-bromo-5-fluoropyridine (1.86 g, 10 mmol) with 1-( tert -butyl)-4-iodobenzene in 98% yield, showing the scalable ability of this C–H bond arylation protocol. As shown in Scheme , the C–Br bond can be converted to hydrogen, aryl, or alkyne groups by different coupling reactions.…”

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confidence: 99%

C–H Bond Functionalization of (Hetero)aryl Bromide Enabled Synthesis of Brominated Biaryl Compounds

Liu

Wang

et al. 2021

Org. Lett.

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Aryl bromide is one of the most important compounds in organic chemistry, because it is widely used as synthetic building blocks enabling quick access to a wide array of bioactive molecules, organic materials, and polymers via the versatile cutting-edge transformations of C–Br bond. Direct C–H bond functionalization of aryl bromide is considered to be an efficient way to prepare functionalized aryl bromides; however, it is rarely explored possibly due to the relatively low reactivity of aryl bromide toward C–H bond activation. We herein report a palladium-catalyzed coupling reaction between aryl iodide and aryl bromide for preparing brominated biaryl compounds via a silver-mediated C–H bond activation pathway.

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Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling

Mishra

Singh

et al. 2021

J. Org. Chem.

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Glycosyl triazoles have been introduced as efficient ligands for the Cu-catalyzed Sonogashira reaction to overcome the challenges of sideways homocoupling reactions in Cu catalysis in this reaction. The atmospheric oxygen in a sealed tube did not affect the coupling, and no need of complete exclusion of oxygen was experienced in the presence of glycohybrid triazole ligand L3. High product yields were obtained at 130 °C for a variety of substrates including aliphatic and aromatic terminal alkynes and differently substituted aromatic halides including 9-bromo noscapine. In contrast, at room temperature, a very low loading of the L3-Cu catalytic system could produce excellent yields in Glaser coupling including homocoupling and heterocoupling of a variety of aliphatic and aromatic alkynes.

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Utilizing a copper-free Sonogashira reaction in the synthesis of the leukotriene a4 hydrolase modulator batatasin IV

Cited by 4 publications

References 17 publications

Hydrazine Hydrate Accelerates Neocuproine–Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation

Hydrazine Hydrate Accelerates Neocuproine–Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation

C–H Bond Functionalization of (Hetero)aryl Bromide Enabled Synthesis of Brominated Biaryl Compounds

Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling

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