Synthesis of 1,4-dithiins and 1,4-diselenins from alkynes and elemental sulfur/selenium under transition metal-free conditions with high regioselectivity

Liu, Cheng; Wang, Mengdan; Gu, Yingge; He, Ping; Wang, Zongkang; Zhuang, Zhiqiang; Kong, Lingkai; Li, Yanzhong

doi:10.1039/d3qo00364g

Cited by 9 publications

(2 citation statements)

References 47 publications

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“…First of all, 5w-1 can be obtained with alkyne and S 8 as starting materials in the presence of K 2 CO 3 (Scheme a). Raising the temperature under the above conditions, Se powder could lead to the corresponding product 5w-2 (Scheme b) . Subsequently, the seven-membered benzo-fused oxacycle 5w-3 was also readily achieved in 61% yield between the reaction of ynone 5w and 2-phenylacetonitrile with t BuOLi as the base (Scheme c).…”

Section: Resultsmentioning

confidence: 99%

“…Raising the temperature under the above conditions, Se powder could lead to the corresponding product 5w-2 (Scheme 7b). 23 Subsequently, the seven-membered benzo-fused oxacycle 5w-3 was also readily achieved in 61% yield between the reaction of ynone 5w and 2phenylacetonitrile with t BuOLi as the base (Scheme 7c). With the assistance of KOH, ynone 5w reacted smoothly with 2-Scheme 5.…”

Section: Journal Of Thementioning

confidence: 99%

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Palladium-Catalyzed Difluorocarbene Transfer Enabled Divergent Synthesis of γ-Butenolides and Ynones from Iodobenzene and Terminal Alkynes

Sheng,

Chen,

Song

2024

J. Am. Chem. Soc.

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Herein, we report a ligand-controlled palladiumcatalyzed method that enables the synthesis of ynones and γbutenolides with excellent regioselectivity from the same set of readily available aryl iodides, aryl acetylenes, and BrCF 2 CO 2 K. In this reaction, the [Pd II ]�CF 2 does demonstrate electrophilicity and can generate CO readily when reacting with H 2 O. It is environmentally friendly and safe compared to traditional methods, and the current protocol enables us to afford ynones and γbutenolides in high yields with excellent functionality tolerance. Moreover, esters can also be obtained with corresponding phenols and alcohols utilizing this strategy. The success of late-stage functionalization of bioactive compounds further illustrates the synthetic utility of this protocol in material development and drug discovery.

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Section: Resultsmentioning

confidence: 99%

Section: Journal Of Thementioning

confidence: 99%

Palladium-Catalyzed Difluorocarbene Transfer Enabled Divergent Synthesis of γ-Butenolides and Ynones from Iodobenzene and Terminal Alkynes

Sheng,

Chen,

Song

2024

J. Am. Chem. Soc.

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Synthesis of Vinyl Sulfones and Benzoxathiins via Base‐Catalyzed Reactions of o‐Hydroxyaryl Thiosulfonates and Ynones

Tang,

Zhang,

Luo

et al. 2024

Adv Synth Catal

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The cyclization reaction and hydrosulfonylation reaction of ynones have been simultaneously realized through a single operation. Under the mediation of cesium carbonate, different S‐(α‐hydroxyaryl) aryl thiosulfonates reacted with various ynones to produce functionalized vinyl sulfones in 37%‐83% yields with E‐selectivity. At the same time, a variety of benzoxathiins were formed in 42%‐97% yields.

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Recent Developments in Selenylation of Alkynes

Xu,

Huang,

et al. 2024

Adv Synth Catal

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Alkynes are simple yet important organic feedstocks. The selenylation of alkynes is able to produce complex selenium‐containing compounds in a facile way. Although there are some reviews about the selenylation of alkynes, most of them focus on one specific reaction or what types of products that can be obtained. There is a lack of attention given to the various uses of different selenium reagents and their mechanisms. This review mainly focuses on recent advances (2013‐2023) based on diverse selenium reagents. Mechanisms and how the added reagents work will be discussed. Different reaction types, including difunctionalization, Se‐annulation, spiro‐cyclization, C‐Se coupling, click reaction will be recorded in this review. The regioselectivity can be achieved through various mechanisms, including radicals, seleniraniums or electrophilic cyclization. We hope it will do help for future research in this area.

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Synthesis of 1,4-dithiins and 1,4-diselenins from alkynes and elemental sulfur/selenium under transition metal-free conditions with high regioselectivity

Abstract: A straightforward protocol for the synthesis of various 1,4-dithiines and 1,4-diselenin starting from alkynes and Elemental sulfur/selenium under transition-metal-free conditions has been demonstrated. This methodology efficiently constructs a broad range...

Cited by 9 publications

References 47 publications

Palladium-Catalyzed Difluorocarbene Transfer Enabled Divergent Synthesis of γ-Butenolides and Ynones from Iodobenzene and Terminal Alkynes

Palladium-Catalyzed Difluorocarbene Transfer Enabled Divergent Synthesis of γ-Butenolides and Ynones from Iodobenzene and Terminal Alkynes

Synthesis of Vinyl Sulfones and Benzoxathiins via Base‐Catalyzed Reactions of o‐Hydroxyaryl Thiosulfonates and Ynones

Recent Developments in Selenylation of Alkynes

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