Direct C–H Sulfonylimination of Pyridinium Salts

Luo, Lihua; Tang, Juan; Sun, Rui; Li, Wenjing; Zheng, Xueli; Yuan, Mao-Ling; Li, Ruixiang; Chen, Hua; Fu, Haiyan

doi:10.1021/acs.orglett.2c00725

Cited by 12 publications

(13 citation statements)

References 37 publications

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“…20 Although 1-methylpyridinium iodide (2b) underwent nucleophilic addition and elimination with tosyl azide in the presence of K 2 CO 3 , generating 1-methyl-2-tosylimino-1,2-dihydropyridine, it did not react under our standard conditions, presumably due to different reaction mechanisms being followed. 21…”

Section: Papermentioning

confidence: 99%

Halide-promoted pyridinylation of α-acylmethylides with 2-halo-1-methylpyridinium iodides as reagents

2023

Org. Biomol. Chem.

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Section: Papermentioning

confidence: 99%

Halide-promoted pyridinylation of α-acylmethylides with 2-halo-1-methylpyridinium iodides as reagents

2023

Org. Biomol. Chem.

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“…In addition, polymeric adsorbents for iodomethane adsorption are mainly based on the chemical reaction between the iodomethane and their functional groups, resulting in poor recyclability. Although a pyridinium salt formation reaction between pyridine and iodomethane is an efficient and rapid organic reaction, [16, 17] it has not been employed as a strategy to trap radioactive iodomethane because of the tedious operations, irritating and environmental unfriendliness of pyridine.…”

Section: Introductionmentioning

confidence: 99%

SuFEx‐Enabled Elastic Polysulfates for Efficient Removal of Radioactive Iodomethane and Polar Aprotic Organics through Weak Intermolecular Forces

Wan

et al. 2022

Angew Chem Int Ed

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Capturing radioactive iodomethane and its vapors is a major challenge due to its low adsorption capacity. Herein, we have developed for the first time a pyridine‐entrapped elastic crosslinked polysulfate gel (pyridine/TPC‐cPS) as an efficient absorbent for iodomethane capture. Each pyridine‐encased TPC‐cPS network cell acts as a mini‐reactor for salt formation between pyridine and iodomethane. The yield reaches up to 96.65 % and traps saturated iodomethane vapor of 1.573 g gpyridine/TPC‐cPS−1 (equivalent to 18.103 g gTPC‐cPS−1), which is the highest capacity reported to date. Both experiments and molecular dynamics simulations reveal that the unusual adsorption of polysulfate for polar aprotic organics can be attributed to the fact that the electrostatic interactions between the polar group (O=S=O) in the polymer backbone and the polar groups in the organic molecules fixed the solvent in the polymer matrix, while the van der Waals forces between the nonpolar groups in the polymer and molecules induced swelling.

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“…In addition, polymeric adsorbents for iodomethane adsorption are mainly based on the chemical reaction between the iodomethane and their functional groups, resulting in poor recyclability. Although a pyridinium salt formation reaction between pyridine and iodomethane is an efficient and rapid organic reaction, [16,17] it has not been employed as a strategy to trap radioactive iodomethane because of the tedious operations, irritating and environmental unfriendliness of pyridine.…”

Section: Introductionmentioning

confidence: 99%

SuFEx‐Enabled Elastic Polysulfates for Efficient Removal of Radioactive Iodomethane and Polar Aprotic Organics through Weak Intermolecular Forces

Wan¹,

Xu²,

Wu³

et al. 2022

Angewandte Chemie

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Capturing radioactive iodomethane and its vapors is a major challenge due to its low adsorption capacity. Herein, we have developed for the first time a pyridine-entrapped elastic crosslinked polysulfate gel (pyridine/TPC-cPS) as an efficient absorbent for iodomethane capture. Each pyridine-encased TPC-cPS network cell acts as a mini-reactor for salt formation between pyridine and iodomethane. The yield reaches up to 96.65 % and traps saturated iodomethane vapor of 1.573 g g pyridine/TPC-cPS À 1 (equivalent to 18.103 g g TPC-cPS À 1 ), which is the highest capacity reported to date. Both experiments and molecular dynamics simulations reveal that the unusual adsorption of polysulfate for polar aprotic organics can be attributed to the fact that the electrostatic interactions between the polar group (O=S=O) in the polymer backbone and the polar groups in the organic molecules fixed the solvent in the polymer matrix, while the van der Waals forces between the nonpolar groups in the polymer and molecules induced swelling.

show abstract

Direct C–H Sulfonylimination of Pyridinium Salts

Cited by 12 publications

References 37 publications

Halide-promoted pyridinylation of α-acylmethylides with 2-halo-1-methylpyridinium iodides as reagents

Halide-promoted pyridinylation of α-acylmethylides with 2-halo-1-methylpyridinium iodides as reagents

SuFEx‐Enabled Elastic Polysulfates for Efficient Removal of Radioactive Iodomethane and Polar Aprotic Organics through Weak Intermolecular Forces

SuFEx‐Enabled Elastic Polysulfates for Efficient Removal of Radioactive Iodomethane and Polar Aprotic Organics through Weak Intermolecular Forces

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