Air-triggered, catalyst-free decarboxylative oxysulfonylation of arylpropiolic acids with sodium sulfinates

Chen, Xingyu; Chang, Xiaoqiang; Zhang, Shuaichen; Lu, Sixian; Liu, Yang; Sun, Peng

doi:10.1007/s10311-022-01440-x

Cited by 5 publications

(1 citation statement)

References 43 publications

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“…The hydro-functionalization of 1, 3-dienes offers convenient approaches to complex allylic compounds. [28][29][30][31][32][33] In 2019, Chatterjee's group reported a hydrothiolation of 1, 3-dienes that yielded 1, 2-Markovnikov sulfide products. These products could be oxidized to produce branched allylic sulfones (Scheme 1a).…”

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confidence: 99%

Catalyst- and Additive-Free Hydrosulfonylation of 1, 3-Dienes for Allylic Sulfones Synthesis

Zhang,

Chang,

Ren

et al. 2024

Preprint

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The demand for environmentally-friendly processes in organic synthesis has spurred interest in developing catalyst- and additive-free reactions for the synthesis of valuable organic compounds. Among these, allylic sulfones are a crucial structural motif used in drug development and organic synthesis. Despite several catalytic protocols have been established for the synthesis of allylic sulfones in recent years, the catalyst- and additive-free process has yet to be explored. In this study, we report a highly efficient and green pro-tocol for the synthesis of allylic sulfones from aryl-1, 3-dienes and sulfinic acids. The reaction was conducted under mild conditions using an aerobic atmosphere at room temperature without any catalyst or additive. The procedure demonstrated excellent atom economy, good regio- and chemo-selectivity, simple operation, and scalability. Overall, this method provides a promising strategy for the synthesis of allylic sulfones in a sustainable and cost-effective manner.

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confidence: 99%

Catalyst- and Additive-Free Hydrosulfonylation of 1, 3-Dienes for Allylic Sulfones Synthesis

Zhang,

Chang,

Ren

et al. 2024

Preprint

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Synthesis of branched allylic sulfones by regioselective boron-catalysed hydrosulfonylation

et al. 2023

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Branched allylic sulfones are privileged scaffolds widely distributed in bioactive molecules, and organic functional materials. Some methods for the synthesis of allyl sulfones have been developed, such as Tsuji-Prost reaction, hydrosulfonylation and radical addition reactions. Despite these advances, the transition-metal-free hydrosulfonylation of unactive 1,3-diene leading to branched allylic sulfones has rarely explored.Herein, a boron-catalysed highly regioselective hydrosulfonylation of 1,3-diene with sul nic acid has been explored to construct a broad scope of branched allylic sulfones. The reactions proceed smoothly without the help of transition-metal-catalyst. Abundant structural motifs have also been obtained through simple transformation from the generated allylic sulfone products.Compared with the previous methods, this protocol exhibited advantages as following: 1) readily available starting material without pre-treatment; 2) under the catalysis of inexpensive boron tri uoride etherate, avoidance of transition-metal-catalyst; 3) simple operation and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger; 4) excellent atom economy and regioselectivity.

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Visible light-driven α-sulfonylation of ketone-derived silyl enol ethers via an electron donor–acceptor complex

Saxena,

Patel,

Sharma

2024

Green Chem.

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Air-triggered, catalyst-free decarboxylative oxysulfonylation of arylpropiolic acids with sodium sulfinates

Cited by 5 publications

References 43 publications

Catalyst- and Additive-Free Hydrosulfonylation of 1, 3-Dienes for Allylic Sulfones Synthesis

Catalyst- and Additive-Free Hydrosulfonylation of 1, 3-Dienes for Allylic Sulfones Synthesis

Synthesis of branched allylic sulfones by regioselective boron-catalysed hydrosulfonylation

Visible light-driven α-sulfonylation of ketone-derived silyl enol ethers via an electron donor–acceptor complex

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