Inorganic sulfites as the sulfur dioxide surrogates in sulfonylation reactions

Ye, Shengqing; Qiu, Guanyinsheng; Wu, Jie

doi:10.1039/c8cc09250h

Cited by 215 publications

(53 citation statements)

References 91 publications

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“…These limitations have been overcome by the introduction of bench-stable and easy-to-handle solid sulfur dioxide surrogates like inorganic sulfites and DABSO. [11,12] DABSO, a charge transfer complex of SO 2 and DABCO, was initially developed by Willis and co-workers for aminosulfonylation. [12a] Subsequently, Wu pioneered the use of DABSO for the generation of aryl sulfonyl radicals which were shown to partake in a variety of elegant transformations.…”

Section: Introductionmentioning

confidence: 99%

Metal Free Sulfonylative Spirocyclization of Alkenyl and Alkynyl Amides via Insertion of Sulfur Dioxide

et al. 2019

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Herein, we report an efficient synthesis of azaspiro[4,5]‐decanes and azaspiro[4,5]‐trienones by the radical cascade spirocyclization of N‐benzylacrylamides or N‐arylpropiolamides respectively. These reactions proceed under metal free conditions and involve in situ generation of aryl sulfonyl radicals from DABSO and aryl diazonium salts. Furthermore, a catalyst free visible light mediated protocol was developed for the sulfonylative spirocyclization of N‐aryl alkynamides using diaryliodonium salts. The utility of these protocols were justified by the excellent compatability of a wide range of functional groups, good yields and scalablity under mild conditions at room temperature.

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Section: Introductionmentioning

confidence: 99%

Metal Free Sulfonylative Spirocyclization of Alkenyl and Alkynyl Amides via Insertion of Sulfur Dioxide

et al. 2019

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“…DABSO as the SO 2 source is stable and reliable, which is an excellent substitute for sulfur dioxide [48] . Metal‐free‐catalyzed multicomponent aminosulfonylation of aryldiazonium tetrafluoroborates with DABSO and hydrazines [49] to synthesize 3‐sulfonated coumarins were reported by Wu and co‐workers [50] …”

Section: Multicomponent Reactions Involving Inorganic Sulfur Componentmentioning

confidence: 99%

Recent Advances in Multicomponent Reactions with Organic and Inorganic Sulfur Compounds

Tang

Yin

Kuchukulla

et al. 2021

The Chemical Record

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In recent years, multicomponent reactions with inorganic and organic sulfur compounds as one of reactants have achieved a remarkable development. In this review, we summarize recent advances in the multicomponent reactions involving sulfur components, which include elemental sulfur, sodium metabisulfite, sodium hyposulfite, potassium pyrosulfite, DABSO, sodium sulfide, thiocyanate, sulfur dioxide, carbon disulfide and other divalent, tetravalent and hexavalent organosulfur compounds.

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“…1,4-Diazabicyclo[2.2.2]octane-bis(sulfur dioxide) adduct (DABSO) as an inexpensive and readily available reagent has been widely used in organic transformations. [116][117][118] In 2019, Chen and coworkers achieved a zinc-mediated intermolecular reductive radical fluoroalkylsulfination of unsaturated C-C bonds with fluoroalkyl bromides and DABSO (Scheme 47). 119 Alkenes and alkynes were all tolerated in this reaction, affording the product with moderate yields.…”

Section: Scheme 38mentioning

confidence: 99%