Photoinduced synthesis of allylic sulfones using potassium metabisulfite as the source of sulfur dioxide

Zhang, Jun; Zhou, Kaida; Qiu, Guanyinsheng; Wu, Jie

doi:10.1039/c8qo01048j

Cited by 57 publications

(19 citation statements)

References 100 publications

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“…Thus, synthesis of alkynyl sulfones (76) involves the reaction of 4-alkyl Hantzsch esters (75), sodium metabisulfite, and alkynyl bromides under metal-free photo-induced conditions as reported by Wu et al in 2020 (Scheme 65). 83 This transformation proceeds smoothly under visible light irradiation at room temperature, giving rise to the corresponding alkyl alkynyl sulfones (76) in moderate to good yields. Besides this, a broad range of substrate scope with good functional group tolerance are other merits of the methodology.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…A broad reaction scope covering alkyl and aryl halides was demonstrated, and various sensitive functional groups such as amino and ester groups were well tolerated (Scheme 56). 76 Scheme 56 Visible-light-mediated synthesis of aryl/alkyl sulfonamides Following the recent trends in C(sp 3 )-H functionalization for sulfonylation, the Wu group demonstrated a visible-light-mediated sulfonylation of 2,4,6-trimethylphenol (67) using sodium metabisulfite (Na 2 S 2 O 5 ) as the SO 2 surrogate. Although the result is interesting, the substrate scope was limited and only 4-methyl phenols with a methyl or tert-butyl group attached to the ortho-position are suitable for this transformation.…”

Section: Scheme 53 Proposed Mechanism For the Formation Of Sulfonamidesmentioning

confidence: 99%

“…A broad reaction scope covering alkyl and aryl halides was demonstrated, and various sensitive functional groups such as amino and ester groups were well tolerated (Scheme 56). 76…”

Section: Synthesis Of 3-(methylsulfonyl)benzo[b]thiophenesmentioning

confidence: 99%

“…Subsequently, addition of alkyl sulfonyl radical (75d) to the alkynyl bromide produces a vinyl radical intermediate (75e). With the assistance of excited photocatalyst, a vinyl anion (75f) is formed, which affords the corresponding alkylalkynyl sulfone (76) with the release of bromide anion (Scheme 66). Scheme 66.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

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The Renaissance of Alkali Metabisulfites as SO2 Surrogates

Patel¹,

Sahoo²,

Dahiya³

et al. 2021

SynOpen

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The upsurge of interest in the development of methodologies for the construction of sulfur-containing compounds via the use of expedient reagents has been established as sustainable tools in organic chemistry. This review focuses on the sulfonylation reactions using inorganic sulfites (Na2S2O5 or K2S2O5) as the sulfur dioxide surrogate. Unlike bis-adduct of DABCO, which is an excellent surrogate of the gaseous SO2, the use of sodium or potassium metabisulfites as SO2 surrogates are equally efficient. The objective of the current review is to bring out the latest collection of sulfonylation reactions using inorganic sulfites. For better understanding, the review is categorized according to the mode of reactions viz., transition metal-catalyzed SO2 insertion, metal-free SO2 insertion, and visible light-mediated SO2 insertion. All the reactions in each of the sections are depicted with selected examples with a pertinent explanation of the proposed mechanism. Nevertheless, based on the biological relevance of sulfonylated compounds the use of inorganic sulfites as the SO2 source in various sulfonylation reactions are needed to be explored.

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Section: Accepted Manuscriptmentioning

confidence: 99%

Section: Scheme 53 Proposed Mechanism For the Formation Of Sulfonamidesmentioning

confidence: 99%

“…A broad reaction scope covering alkyl and aryl halides was demonstrated, and various sensitive functional groups such as amino and ester groups were well tolerated (Scheme 56). 76…”

Section: Synthesis Of 3-(methylsulfonyl)benzo[b]thiophenesmentioning

confidence: 99%

Section: Accepted Manuscriptmentioning

confidence: 99%

See 2 more Smart Citations

The Renaissance of Alkali Metabisulfites as SO2 Surrogates

Patel¹,

Sahoo²,

Dahiya³

et al. 2021

SynOpen

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show abstract

“…The above method was also applied for the synthesis of allylic sulfones through a photoinduced three‐component reaction of aryl/alkyl halides, potassium metabisulfite, and allylic bromides under ultraviolet irradiation at room temperature (Scheme ) . In this reaction, the cheap and abundant potassium metabisulfite was used as the source of sulfur dioxide.…”

Section: Photo‐initiated Formation Of Radical With the Subsequent mentioning

confidence: 99%

Photoinduced Sulfonylation Reactions through the Insertion of Sulfur Dioxide

Xie

et al. 2019

Eur J Org Chem

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Recent advances in the photoinduced sulfonylation reactions through the insertion of sulfur dioxide are summarized. Among the approaches developed in the sulfonylation reactions, the insertion of sulfur dioxide via radical process can be accomplished with the assistance of photoredox catalysis in the presence of visible light or under ultraviolet irradiation, depending the substrates used in the reactions. Under ultraviolet irradiation, the conversion can be completed under metal‐ and additive‐free conditions. It is noteworthy that alkyl halides possessing eliminable β‐hydrogen atom are effective as alkyl radical precursors with the insertion of sulfur dioxide. Two parts, according to the photoinduced reaction pathways, are introduced: (a) photo‐initiated formation of radical with the subsequent capture of sulfur dioxide; (b) photo‐assisted single electron transfer (SET) after insertion of sulfur dioxide. During the transformation, an oxidative or reductive single electron transfer would occur under visible light photoredox catalysis.

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Radical Reactions

Hussaini¹

2023

Organic Reaction Mechanisms Series

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Photoinduced synthesis of allylic sulfones using potassium metabisulfite as the source of sulfur dioxide

Abstract: Synthesis of allylic sulfones through a photoinduced three-component reaction of aryl/alkyl halides, potassium metabisulfite, and allylic bromides under ultraviolet irradiation at room temperature is developed. Diverse allylic sulfones are generated in moderate to good yields.

Cited by 57 publications

References 100 publications

The Renaissance of Alkali Metabisulfites as SO2 Surrogates

The Renaissance of Alkali Metabisulfites as SO2 Surrogates

Photoinduced Sulfonylation Reactions through the Insertion of Sulfur Dioxide

Radical Reactions

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