Palladium-catalyzed cross-coupling of alkylindium reagent with diaryliodonium salt

Li, Wenxin; Yang, Bo-Wen; Na, Jin-He; Rao, Weidong; Chu, Xiangcheng; Shen, Zhi‐Liang

doi:10.1016/j.tetlet.2022.153729

Cited by 4 publications

(3 citation statements)

References 51 publications

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“…1 H NMR (400 MHz, CDCl 3 ) δ 7.35-7.28 (m, 2H), 7.26-7.19 (m, 3H), 7.05 (d, J = 7.6 Hz, 1H), 7.00 (d, J = 1.8 Hz, 1H), 6.95 (dd, J = 7.6, 1.8 Hz, 1H), 2.87 (brs, 4H), 2.31 (s, 3H), 2.28 (s, 3H). [21] 1-Methoxy-4-phenethylbenzene (3 e): Compound 3 e was prepared from (E)-1-methoxy-4-styrylbenzene (1 e) in 92% yield as a colorless oil (39.1 mg). 1 H NMR (400 MHz, CDCl 3 ) δ 7.32-7.24 (m, 2H), 7.23-7.15 (m, 3H), 7.10 (d, J = 8.6 Hz, 2H), 6.83 (d, J = 8.6 Hz, 2H), 3.80 (s, 3H), 2.94-2.83 (m, 4H).…”

Section: 2-diphenylethane (3 A)mentioning

confidence: 99%

Nickel‐Catalyzed Transfer Hydrogenation of Unactivated Aryl Alkenes with Hydrosilane as Hydrogen Source

Wang

Xiong

et al. 2022

Asian J Org Chem

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A nickel‐catalyzed transfer hydrogenation of aryl alkenes has been developed using hydrosilane as the hydrogen source. Sterically hindered disubstituted or trisubstituted alkenes were employed to test the efficiency of this transformation. Mechanism studies showed that hydrogenation took place smoothly with more sterically‐hindered trans‐alkenes. While uncongested cis‐alkenes could hardly convert to the alkanes but hydrosilylation products were generated instead. Moreover, certain amount of water was found to be a promotion for the protonation process and could partly serve as the hydrogen source. Not only for simple stilbenes, this easy handle protocol also showed tolerance for substrates involving other unsaturated groups as well as heterocycles.

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Section: 2-diphenylethane (3 A)mentioning

confidence: 99%

Nickel‐Catalyzed Transfer Hydrogenation of Unactivated Aryl Alkenes with Hydrosilane as Hydrogen Source

Wang

Xiong

et al. 2022

Asian J Org Chem

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“…Palladium is a noble metal of the platinum group and is widely used in various fields of science and technology. For example, palladium is used in electronics as part of multilayer ceramic capacitors of printed circuit boards [ 1 ], in the automotive industry in catalytic converters in cars [ 2 ], as well as in jewelry [ 3 ], chemical catalysis [ 4 , 5 ], and hydrogen energy production [ 6 ]. However, the content of palladium in natural deposits of platinum group metals is extremely low.…”

Section: Introductionmentioning

confidence: 99%

Extraction of Palladium(II) with a Magnetic Sorbent Based on Polyvinyl Alcohol Gel, Metallic Iron, and an Environmentally Friendly Polydentate Phosphazene-Containing Extractant

Yudaev

Butorova

Степанов

et al. 2022

Gels

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In this work, a highly efficient and environmentally friendly method for extracting palladium from hydrochloric acid media was developed. The method uses a magnetic sorbent carrying an organophosphorus extractant, which is not washed from the sorbent into the aqueous phase. The extractant was characterized by 1H, 13C, and 31P NMR spectroscopy and MALDI TOF mass spectrometry, and the palladium complex based on it was characterized by IR spectroscopy. According to an in vitro microbiological study, the extractant was non-toxic to soil microflora. It was established that the water uptake and saturation magnetization of the magnetic sorbent were sufficient for use in sorption processes. The sorption efficiency of palladium(II) with the developed sorbent can reach 71% in one cycle. After treatment of the spent sorbent with 5 M hydrochloric acid, palladium was completely extracted from the sorbent. The new sorbent is proposed for the extraction of palladium from hydrochloric acid media obtained by the leaching of electronic waste.

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“…We also wonder whether a heterocyclic phosphonium salt could serve as a new type of coupling partner for Pd-catalyzed Sonogashira coupling reactions. In continuation of our interest in developing cross-couplings with the use of alternative electrophilic coupling partners, herein we report an efficient Pd/Cu-catalyzed Sonogashira reaction of a heterocyclic phosphonium salt with a terminal alkyne via C–P bond cleavage, which proceeded smoothly to give the corresponding alkynyl-substituted pyridine, quinoline, pyrazine, and quinoxaline in modest to good yields with good substrate generality and wide functional group compatibility (Scheme b).…”

mentioning

confidence: 99%

Palladium-Catalyzed Sonogashira Coupling of a Heterocyclic Phosphonium Salt with a Terminal Alkyne

Zhang

Wang

et al. 2022

Org. Lett.

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An efficient Sonogashira coupling of a heterocyclic phosphonium salt with a terminal alkyne via C–P bond cleavage was developed. The reactions proceeded smoothly in the presence of palladium catalyst, copper(I) iodide, and N,N-diisopropylethylamine (DIPEA) in N-methyl-2-pyrrolidone (NMP) at 100 °C for 12 h, producing the corresponding alkynyl-substituted pyridine, quinoline, pyrazine, and quinoxaline in moderate to good yields with wide substrate scope and broad functional group tolerance. In addition, gram-scale synthesis could also be achieved, and the reaction could be applied to the functionalization of alkyne-containing complex molecules derived from sugars and pharmaceutical and naturally occurring products (e.g., estrone, d-galactopyranose, menthol, and ibuprofen).

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Palladium-catalyzed cross-coupling of alkylindium reagent with diaryliodonium salt

Cited by 4 publications

References 51 publications

Nickel‐Catalyzed Transfer Hydrogenation of Unactivated Aryl Alkenes with Hydrosilane as Hydrogen Source

Nickel‐Catalyzed Transfer Hydrogenation of Unactivated Aryl Alkenes with Hydrosilane as Hydrogen Source

Extraction of Palladium(II) with a Magnetic Sorbent Based on Polyvinyl Alcohol Gel, Metallic Iron, and an Environmentally Friendly Polydentate Phosphazene-Containing Extractant

Palladium-Catalyzed Sonogashira Coupling of a Heterocyclic Phosphonium Salt with a Terminal Alkyne

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