A Convenient Multigram Synthesis of DABSO Using Sodium Sulfite as SO<sub>2</sub> Source

Mileghem, Seger Van; Borggraeve, Wim M. De

doi:10.1021/acs.oprd.7b00083

Cited by 22 publications

(13 citation statements)

References 23 publications

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“…The increasing emission of SO 2 from the burning of fossil fuels has drawn much attention because it is a significant source of atmospheric pollution that threatens the environment and human health. Millions of tons of SO 2 are produced every year, , and its primary utilization is as a feedstock in the industrial preparation of sulfuric acid, amino sulfonamides, sulfones, and metal sulfite salts. − Up to now, SO 2 capture and utilization (SCU) are still highly desirable from the viewpoint of sustainable chemistry and economic perspectives. For the removal of SO 2 , although many conventional methods had been developed, they are always accompanied by some inevitable shortcomings. , For example, limestone scrubbing is irreversible and results in huge amounts of CaSO 4 and wastewater, leading to secondary pollution to the environment .…”

Section: Introductionmentioning

confidence: 99%

Efficient SO₂ Capture and Fixation to Cyclic Sulfites by Dual Ether-Functionalized Protic Ionic Liquids without Any Additives

Zhao

Zhang

et al. 2018

ACS Sustainable Chem. Eng.

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The capture of SO 2 with ionic liquids (ILs) has attracted much attention in recent years; however, the examples involving SO 2 capture and utilization (SCU) in the same medium are scarce. Here, we demonstrated an innovative strategy for SO 2 capture and fixation to cyclic sulfites in dual ether-functionalized protic ionic liquids (PILs) for the first time. These dual ether-functionalized PILs exhibited low viscosities and remarkable SO 2 loading capacities (up to 6.12 mol of SO 2 per mol of IL and 1.34 g of SO 2 per g of IL at 1.0 bar) that is conducive to conversion of SO 2 absorbed in situ. The mechanism of absorption was proposed which includes both chemical and physical absorptions from the spectral results and theoretical calculations. Particularly, the SO 2 absorbed in the PILs was directly transformed into cyclic sulfites without any additives; meanwhile, these PILs were also used as efficient catalysts for the synthesis of a series of cyclic sulphites using equimolar SO 2 and epoxides. Good to excellent yields of cyclic sulfites were obtained for varied substrates. The dual roles of PILs as both absorbents and catalysts as well as the recyclability of the PILs are examined in detail in this paper. This innovative strategy not only eliminated the traditional intensive energy input for SO 2 desorption but also enabled the production of value-added cyclic sulfites.

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Section: Introductionmentioning

confidence: 99%

Efficient SO₂ Capture and Fixation to Cyclic Sulfites by Dual Ether-Functionalized Protic Ionic Liquids without Any Additives

Zhao

Zhang

et al. 2018

ACS Sustainable Chem. Eng.

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“…[28] The SO 2 gas is produced by the reaction of sodium sulphite and concentrated H 2 SO 4 in the left chamber. It is diffused to the other arm through the connector for hydro‐ and alkoxyarylsulfonylation reaction affording moderate to good yields of the desired products [29] . This experiment demonstrates that SO 2 gas is capable to react with diazonium salt even in the absence of DABCO.…”

Section: Figurementioning

confidence: 83%

Metal‐Free, Multicomponent Anti‐Markovnikov Hydroarylsulfonylation and Alkoxyarylsulfonylation of Vinyl Arenes

Das

Varalaxmi

et al. 2020

Adv Synth Catal

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A unified strategy for the hydro‐arylsulfonylation of vinyl arenes has been developed under catalyst, additive‐free conditions at room temperature from the corresponding aryldiazonium salts, DABSO (DABCO ⋅ 2SO2), and thiophenol as hydrogen atom transfer (HAT) reagent. Mechanistically, an incipient arylsulfonyl radical is generated from the corresponding aryl diazonium salts and DABSO which undergoes anti‐Markovnikov addition to styrenes followed by hydrogen atom transfer from thiophenol. Interestingly, this multi‐component reaction is highly chemoselective suppressing deleterious thiosulfonylation and thiol‐ene reactions. Tuning the reaction conditions, a four‐component difunctionalization with alkoxy group has been achieved using 1,4‐dicyanobenzene as an oxidant. Furthermore, base‐promoted elimination to form vinyl sulfone has been also examined. The practicability of this present reaction has been demonstrated by the ex situ generation of sulfur dioxide in an H‐type reaction vessel and subsequent hydro‐ and alkoxyarylsulfonylation in good to moderate yields. The hydroarylsulfonylation reaction is scalable and applied to a metal‐free synthesis of the key intermediate for an anti‐migraine drug Eletriptan.

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“…5 DABSO can be readily prepared by refluxing DABCO in liquid SO 2 (Scheme 1 ), 6 although alternative preparations have been developed using the Karl Fischer reagent 7 or by using sodium sulfite as the source of SO 2 . 8 It is available commercially from multiple vendors. Due to its ease of preparation, favorable physical properties, and high proportion (>50%) of its molecular weight as SO 2 , DABSO was identified as an ideal choice to study the use of amine–SO 2 Lewis adducts as SO 2 surrogates.…”

Section: Dabsomentioning

confidence: 99%

DABSO – A Reagent to Revolutionize Organosulfur Chemistry

Willis¹,

Andrews²

2022

Synthesis

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The introduction of easy-to-handle SO2 surrogates has transformed the field of sulfur chemistry, enabling methodologies utilizing SO2 to be carried out without specialized apparatus, and paving the way for the development of new procedures. This review highlights some of the varied and significant developments associated with one of the most prominent SO2 surrogates: DABSO.1 Introduction2 DABSO3 Reactions with Nucleophilic Reagents4 Metal-Catalyzed Reactions4.1 Palladium-Catalyzed Reactions4.2 Other Transition-Metal Catalysis5 Radical Reactions5.1 Aryldiazonium Salts5.2 Other Aryl Radical Precursors5.3 Alkyl Radical Precursors6 Conclusion

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A Convenient Multigram Synthesis of DABSO Using Sodium Sulfite as SO₂ Source

Abstract: A convenient multigram synthesis of DABSO using sodium sulfite as SO2 source

Cited by 22 publications

References 23 publications

Efficient SO₂ Capture and Fixation to Cyclic Sulfites by Dual Ether-Functionalized Protic Ionic Liquids without Any Additives

Efficient SO₂ Capture and Fixation to Cyclic Sulfites by Dual Ether-Functionalized Protic Ionic Liquids without Any Additives

Metal‐Free, Multicomponent Anti‐Markovnikov Hydroarylsulfonylation and Alkoxyarylsulfonylation of Vinyl Arenes

DABSO – A Reagent to Revolutionize Organosulfur Chemistry

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A Convenient Multigram Synthesis of DABSO Using Sodium Sulfite as SO2 Source

Abstract: A convenient multigram synthesis of DABSO using sodium sulfite as SO2 source

Cited by 22 publications

References 23 publications

Efficient SO2 Capture and Fixation to Cyclic Sulfites by Dual Ether-Functionalized Protic Ionic Liquids without Any Additives

Efficient SO2 Capture and Fixation to Cyclic Sulfites by Dual Ether-Functionalized Protic Ionic Liquids without Any Additives

Metal‐Free, Multicomponent Anti‐Markovnikov Hydroarylsulfonylation and Alkoxyarylsulfonylation of Vinyl Arenes

DABSO – A Reagent to Revolutionize Organosulfur Chemistry

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Product

Resources

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A Convenient Multigram Synthesis of DABSO Using Sodium Sulfite as SO₂ Source

Efficient SO₂ Capture and Fixation to Cyclic Sulfites by Dual Ether-Functionalized Protic Ionic Liquids without Any Additives

Efficient SO₂ Capture and Fixation to Cyclic Sulfites by Dual Ether-Functionalized Protic Ionic Liquids without Any Additives