Why chemists can’t quit palladium

Remmel, Ariana

doi:10.1038/d41586-022-01612-3

Cited by 6 publications

(6 citation statements)

References 11 publications

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“…Column chromatography was performed using silica gel (60−200 μm, 60 Å) from Fisher Scientific. The 1 H NMR and 13 C NMR (δ in parts per million) spectra were recorded using a Bruker 300 MHz spectrometer in CDCl 3 or DMSO-d 6 . The MS spectra were collected on LC-MS-Shimadzu-2020.…”

Section: Materials and Instrumentationmentioning

confidence: 99%

“…The residue was purified by silica gel column chromatography (hexane: ethyl acetate of 6:1) to produce compound 2 (0.41 g, 80%) as a light yellow solid. 1 H NMR and 13 C NMR spectra are shown in Figures S2 and S3 in the Supporting Information. 1 H NMR (300 MHz, CDCl 3 ): δ (×10 −6 ): 0.99 (t, J = 7.3 Hz, 3H), 1.42−1.52 (m, 2H), 1.68−1.78 (m, 2H), 4.17…”

Section: Synthesis Of N-butyl-4-alloxy-18-naphthalimide (Compound 2)mentioning

confidence: 99%

“…12 In the same time, researchers tried to develop Pd-free catalysts for coupling reactions, but later found that the reagents were contaminated by trace palladium. 13 In addition, palladium species bind to various biomolecules such as proteins and nucleic acids, leading to a range of physiological dysfunctions and negatively affecting human health. 14,15 Thus, the development of simple and reliable sensors to monitor palladium with extremely high sensitivity and selectivity is required.…”

Section: ■ Introductionmentioning

confidence: 99%

“…13 C NMR (300 MHz, CDCl 3 ): δ (×10−6 ): 13.88, 20.42, 30.27, 40.10, 69.55, 106.20, 115.20, 118.72, 122.46, 123.57, 125.92, 128.63, 129.41, 131.52, 131.87, 133.27, 159.61, 163.93, 164.51. MS (ESI + ) calcd for C 19 H 19 NO 3 [M + H] + , 310.14; found, 310.05.…”

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confidence: 99%

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Reaction-Based Multisignal Detection of Palladium with High Sensitivity, Selectivity, and Reliability

Mosleh,

Hardaker,

Bartolini

et al. 2024

ACS Appl. Opt. Mater.

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Due to vast application of palladium in academia and industry and its toxicity, it is critical to develop user-friendly, portable, and affordable methods for accurately detecting ultratrace Pd. In this study, a highly sensitive and selective fluorescent probe (N-butyl-4-alloxy-1,8-naphthalimide, compound 2) was synthesized, which demonstrated multiple signals [enhanced fluorescence (FL), ratiometric FL, and colorimetric responses] upon interaction with palladium. The compound 2 was designed by incorporating a naphthalimidebased fluorescent dye as the fluorophore and an allyl ether group as a responsive unit. Utilizing a Pd 0 -triggered cleavage reaction by a deallylation reaction through the Tsuji−Trost reaction, compound 2 exhibited rapid response, wide linearity, exceptional sensitivity with a limit of detection as low as 2.2 pM, and high selectivity toward palladium species. In addition, as a ratiometric and enhanced FL response, the probe could be developed as a portable sensor via naked eye visualization for semiquantitative and selective detection of palladium. Integrating with an easily available smartphone (with a camera and a color-analysis app), potential in situ quantitative detection was achieved at a low cost. The probe shows multiple signals for palladium detection and potential as a portable sensor, and this work provides valuable insights into developing sensors with good sensitivity, selectivity, improved reliability, and portability for detection of palladium and other analytes of interest.

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Section: Materials and Instrumentationmentioning

confidence: 99%

Section: Synthesis Of N-butyl-4-alloxy-18-naphthalimide (Compound 2)mentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Reaction-Based Multisignal Detection of Palladium with High Sensitivity, Selectivity, and Reliability

Mosleh,

Hardaker,

Bartolini

et al. 2024

ACS Appl. Opt. Mater.

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“…Since the organohalide coupling partners are not environmentally friendly and naturally abundant, − the widely available carboxylic acids and sulfones are utilized to replace the organohalides, and the decarbonylative and desulfonative SMC reactions have been developed (Scheme ). − Recently, the breakthrough was made on the base-free Ni-catalyzed SMC reactions to avoid the expensive and toxic Pd catalysts. − Although these accomplished achievements, developing efficient catalytic SMC reactions to meet the requisite costs and energy metrics is still a critical task. , Understanding the mechanisms of SMC reactions is crucial for developing new catalysts with better performance.…”

Section: Introductionmentioning

confidence: 99%

Unveiling Pre-Transmetalation Intermediates in Base-Free Suzuki–Miyaura Cross-Couplings: A Computational Study

Xie,

Zhang,

Song

et al. 2024

Inorg. Chem.

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The pre-transmetalation intermediates are critically important in Suzuki−Miyaura cross-coupling (SMC) reactions and have become a hot spot of the current research. However, the pretransmetalation intermediates under base-free conditions have not been clear. Herein, a comprehensive theoretical study is performed on the base-free Pd-catalyzed desulfonative SMC reaction. The fragile coordination feature and the acceleration role of the RuPhos chelate ligand are revealed. The hydrogen-bond complex between the Pd−F complex and aryl boronic acid is identified as an important pre-transmetalation intermediate, which increases the energy span to 32.5 kcal/mol. The controlling factor for the formation of the hydrogen-bond complexes is attributed to the electronegativities of halogen atoms in the metal halide complexes. What is more, other reported SMC reaction systems involving metal halide complexes and aryl boronic acids are reconsidered and suggest that the hydrogen-bond complexes widely exist as stable pre-transmetalation intermediates with influencing the catalytic activities. The earth-abundant Ni-catalyzed desulfonative SMC reaction is further designed and predicted to have a higher activity than the original Pd-catalyzed SMC reaction.

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Recent Advances in the Nickel‐catalysed Electrochemical Coupling Reactions with a Focus on the Type of Bond Formed

Jose¹,

Diana²,

Kanchana³

et al. 2023

Asian J Org Chem

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Despite being around for many decades, electrochemical metal catalysis has recently widened the realm of electrochemical synthesis by merging sustainable electrosynthesis and tremendous metal catalysis. As the electric current can be controlled to stimulate the development of reactive intermediates and catalysts without the use of external oxidising or reducing agents and considering that it is more selective, generates less waste, and works under reasonable conditions, this strategy represents an eco-friendly and economically sustainable method. Nickel can be used efficiently in electrochemical metal-catalysed reactions owing to its inexpensive nature, high reactivity towards less reactive electrophiles and unique single electron transfer (SET) catalytic cycle. This review covers the recent advances in nickel-catalysed electrochemical coupling reactions from 2017 to 2022, with a focus on different reactions that forge CÀ C or C-heteroatom bonds.

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Why chemists can’t quit palladium

Cited by 6 publications

References 11 publications

Reaction-Based Multisignal Detection of Palladium with High Sensitivity, Selectivity, and Reliability

Reaction-Based Multisignal Detection of Palladium with High Sensitivity, Selectivity, and Reliability

Unveiling Pre-Transmetalation Intermediates in Base-Free Suzuki–Miyaura Cross-Couplings: A Computational Study

Recent Advances in the Nickel‐catalysed Electrochemical Coupling Reactions with a Focus on the Type of Bond Formed

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