Electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides: access to functionalized coumarins or quinolinones

Hua, Jiawei; Fang, Zheng; Xu, Jia; Bian, Mixue; Liu, Chengkou; He, Wei; Zhu, Ning; Zhao, Yang; Guo, Kai

doi:10.1039/c9gc02131k

Cited by 100 publications

(53 citation statements)

References 71 publications

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“…Owing to the relative stabilityo f the resonant free radical and the five-membered ring structure, vinyl radical D tends to undergo the intramolecular spirocyclization to provide E,w hich is clearly different from our earlier work. [12] Additionally,i ntermediate E undergoes further oxidation at the anode to afford oxygenium cation intermediate F.…”

Section: Resultsmentioning

confidence: 99%

“…[11] Inspired by this great breakthrough, the spirocycle formation could be fulfilled in an electrochemical environment. In our previous work, [12] ortho-cyclization of alkynoates and alkynamides with An ovel and green route has been developed for the electrochemicals ynthesis of spiro[4.5]trienones throughr adical-initiated dearomative spirocyclization of alkynesw ith diselenides. This metal-free and oxidant-free electrosynthesis reaction was performed in an undividedc ell under mild conditions.…”

Section: Introductionmentioning

confidence: 99%

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Electrochemical Synthesis of Spiro[4.5]trienones through Radical‐Initiated Dearomative Spirocyclization

et al. 2020

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A novel and green route has been developed for the electrochemical synthesis of spiro[4.5]trienones through radical‐initiated dearomative spirocyclization of alkynes with diselenides. This metal‐free and oxidant‐free electrosynthesis reaction was performed in an undivided cell under mild conditions. A variety of selenation spiro[4.5]trienones products were prepared in moderate‐to‐good yields, showing a broad scope and functional group tolerance. Moreover, the developed continuous‐flow system combined with electrosynthesis possesses the potential to achieve scaled‐up reactions, overcoming the low efficiency of conventional electrochemical scaled‐up reactions.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Electrochemical Synthesis of Spiro[4.5]trienones through Radical‐Initiated Dearomative Spirocyclization

et al. 2020

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“…[63] The alkynoates/alkynamides 77 were forced for direct electrochemical oxidative cyclization with diselenide or disulfide 4 towards the synthesis of the chalcogen functionalized coumarins and quinolinones 78 is shown in Scheme 28. [64]…”

Section: Synthesis Of 3-organochalconyl-2h-coumarinmentioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

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containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se‐heterocycles. The synthesis of seleno‐heterocycles via different nucleophiles including O, N, S, Se, Te, and C‐nucleophiles is exhaustively discussed. Also, one‐pot electrophilic cyclization of 1,3‐diynes and 1,3,5‐triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium‐β‐lactam, carbapenem heterocycle, bis‐ and tris‐selenide alkene, β‐selenosulfonation and selenated alkynes were discussed. The Se‐heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

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“…Subsequently, Liu and co-workers [15] proposed metal-free oxidative radical annulations of propargylic aryl ethers with diselenides. In 2019, Guo and co-workers [16] developed efficient intramolecular annulations of activated alkynes with diselenides or disulfides using constant current electrolysis under metal-free and oxidant-free conditions. The substrate scope was explored using a sequence of alkynoates and alkynamides, which were reacted with diselenides and disulfides to offer the corresponding products.…”

Section: Cà C Bond Formationmentioning

confidence: 99%

Electrochemically Enabled Intramolecular and Intermolecular Annulations of Alkynes

Sun

Liu

et al. 2020

Adv Synth Catal

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Electrosynthesis is recognized as one of the most powerful and sustainable methods in organic chemistry. Recently, electrochemically enabled annulations of carbon‐carbon triple bonds have been successfully achieved, and have broadened prospects for the application of the emerging method with cyclization of alkynes. Thus, herein we outline the recent progress made on electrochemically enabled annulations of alkynes. In addition, an emphasis on the scope, limitations and the mechanisms of these reactions is made in this review.

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Electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides: access to functionalized coumarins or quinolinones

Abstract: A direct electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides toward functionalized coumarins and quinolinones has been developed.

Cited by 100 publications

References 71 publications

Electrochemical Synthesis of Spiro[4.5]trienones through Radical‐Initiated Dearomative Spirocyclization

Electrochemical Synthesis of Spiro[4.5]trienones through Radical‐Initiated Dearomative Spirocyclization

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Electrochemically Enabled Intramolecular and Intermolecular Annulations of Alkynes

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