Green Oxidation of Sulfide to Sulfoxide and Sulfone

Li, Yiming; Jiang, Xuefeng

doi:10.1002/9781119304197.ch12

Cited by 5 publications

(4 citation statements)

References 110 publications

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“…Regrettably, the experimental outcomes did not present a signal peak for acyl fluoride, but a signal of 19 F at À149.71 ppm was observed, which corresponds to the additional product of F À on the carbonyl group of N-sulfonyl succinimide. To ascertain the impact of KF on the 19 F NMR spectrum, a blank control experiment of potassium fluoride was tested with a signal at À125.79 ppm.…”

Section: Resultsmentioning

confidence: 99%

“…Sulfonamides have traditionally been prepared using metal reagents and organocatalysts. 14,[17][18][19] However, several effective oxidation reactions have been reported for synthesizing sulfonamides. 20,21 Unfortunately, these reactions often involve the use of unstable, hazardous, and carcinogenic materials, for example, sulfonyl chlorides or organoazides, 20,22 as well as toxic high-boiling polar solvents that generate significant amounts of toxic waste.…”

Section: Introductionmentioning

confidence: 99%

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An efficient and straightforward approach for accessing sulfonamide/N-sulfonyl succinic esters via potassium fluoride-promoted C–N cleavage of N-sulfonyl succinimide

Lu,

Yang,

Luo

et al. 2024

New J. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

An efficient and straightforward approach for accessing sulfonamide/N-sulfonyl succinic esters via potassium fluoride-promoted C–N cleavage of N-sulfonyl succinimide

Lu,

Yang,

Luo

et al. 2024

New J. Chem.

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“…Although a variety of other oxidants, such as nitric oxide, different metal oxides, hypervalent iodine reagents, halogenates or perhalogenates can be employed for the oxidation of sulfides to sulfones, [13a] these procedures are all problematic in terms of toxic reagents, excess reagents, low chemoselectivity, or the use of hazardous organic solvents. [13b] …”

Section: Synthesis Via the Oxidation Of Sulfidesmentioning

confidence: 99%

Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones

et al. 2021

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Sulfones play a pivotal role in modern organic chemistry. They are highly versatile building blocks and find various applications as drugs, agrochemicals, or functional materials. Therefore, sustainable access to this class of molecules is of great interest. Herein, the goal was to provide a summary on recent develop-ments in the field of sustainable sulfone synthesis. Advances and existing limitations in traditional approaches towards sulfones were reviewed on selected examples. Furthermore, novel emerging technologies for a more sustainable sulfone synthesis and future directions were discussed.

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“…The catalytic oxidation of thioethers is an important research field because sulfoxides and sulfones, the products of thioethers oxidation, are widely used as intermediates in the synthesis of fine chemicals and pharmaceuticals (Madesclaire, 1986;Fernandez and Khiar, 2003;Rostamnia and Mohsenzad, 2018;Li and Jiang, 2019). Moreover, liquid-phase oxidation of S-containing organic compounds is considered as a promising methodology for removal of S-containing compounds from fuels (Campos-Martin et al, 2010) and decontamination of chemical warfare agents (Dong et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

Carbon Nanotubes Modified by Venturello Complex as Highly Efficient Catalysts for Alkene and Thioethers Oxidation With Hydrogen Peroxide

et al. 2019

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In this work, we elaborated heterogeneous catalysts on the basis of the Venturello complex [PO 4 {WO(O 2 ) 2 } 4 ] 3− (PW 4 ) and nitrogen-free or nitrogen-doped carbon nanotubes (CNTs or N-CNTs) for epoxidation of alkenes and sulfoxidation of thioethers with aqueous hydrogen peroxide. Catalysts PW 4 /CNTs and PW 4 /N-CNTs (1.8 at. % N) containing 5-15 wt. % of PW 4 and differing in acidity have been prepared and characterized by elemental analysis, N 2 adsorption, IR spectroscopy, HR-TEM, and HAADF-STEM. Studies by STEM in HAADF mode revealed a quasi-molecular dispersion of PW 4 on the surface of CNTs. The addition of acid during the immobilization is not obligatory to ensure site isolation and strong binding of PW 4 on the surface of CNTs, but it allows one to increase the PW 4 loading and affects both catalytic activity and product selectivity. Catalytic performance of the supported PW 4 catalysts was evaluated in H 2 O 2 -based oxidation of two model substrates, cyclooctene and methyl phenyl sulfide, under mild conditions (25-50 • C). The best results in terms of activity and selectivity were obtained using PW 4 immobilized on N-free CNTs in acetonitrile or dimethyl carbonate as solvents. Catalysts PW 4 /CNTs can be applied for selective oxidation of a wide range of alkenes and thioethers provided a balance between activity and selectivity of the catalyst is tuned by a careful control of the amount of acid added during the immobilization of PW 4 . Selectivity, conversion, and turnover frequencies achieved in epoxidations over PW 4 /CNTs catalysts are close to those reported in the literature for homogeneous systems based on PW 4 . IR spectroscopy confirmed the retention of the Venturello structure after use in the catalytic reactions. The elaborated catalysts are stable to metal leaching, show a truly heterogeneous nature of the catalysis, can be easily recovered by filtration, regenerated by washing and evacuation, and then reused several times without loss of the catalytic performance.

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Green Oxidation of Sulfide to Sulfoxide and Sulfone

Cited by 5 publications

References 110 publications

An efficient and straightforward approach for accessing sulfonamide/N-sulfonyl succinic esters via potassium fluoride-promoted C–N cleavage of N-sulfonyl succinimide

An efficient and straightforward approach for accessing sulfonamide/N-sulfonyl succinic esters via potassium fluoride-promoted C–N cleavage of N-sulfonyl succinimide

Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones

Carbon Nanotubes Modified by Venturello Complex as Highly Efficient Catalysts for Alkene and Thioethers Oxidation With Hydrogen Peroxide

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