Electrochemical oxidative cyclization of olefinic carbonyls with diselenides

Guan, Zhipeng; Wang, Yunkun; Wang, Huamin; Huang, Yuner; Wang, Siyuan; Tang, Hongding; Zhang, Heng; Lei, Aiwen

doi:10.1039/c9gc02665g

Cited by 83 publications

(41 citation statements)

References 72 publications

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“…To the best of our knowledge oxidant free chalcogenation of β,γ ‐unsaturated oxime to form isoxazoline derivative under electrochemical conditions has not been reported so far. Given the importance of oxazoline and isoxazoline moieties, herein we report a sustainable method for the electro‐oxidative chalcogenation of different amides and oximes to synthesize chalcogen‐functionalized heterocycles, in a mediator free undivided electrochemical cell (Scheme ).…”

Section: Figurementioning

confidence: 99%

Electrochemical Chalcogenation of β,γ‐Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines

et al. 2020

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The current report represents a transition‐metal‐free synthesis of oxazoline and isoxazoline derivatives by a tandem electro‐oxidative chalcogenation‐cyclization process. Both C−Se and C−S bond‐forming protocols were developed without using any external oxidant and the reaction was performed at room temperature, open to the air. Using this methodology, 29 substituted oxazoline and 16 substituted isoxazoline derivatives were synthesized with up to 91% isolated yield.

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Section: Figurementioning

confidence: 99%

Electrochemical Chalcogenation of β,γ‐Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines

et al. 2020

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“…Electrochemical anodic oxidation has been utilized for constructing C−C, C−N, C−O and C−S bond, as previously demonstrated by Lin, [35] Mei, [36,37] Zeng, [33] and Lei [38,39] . In particular, electrochemical oxidative selenenylation of alkyne or alkene using diselenides has been successfully demonstrated [40,41] . In 2018, Lei and co‐workers demonstrate the electrochemical oxidative alkoxysulfonylation of alkenes by employing sulfonyl hydrazides and alcohols [42] .…”

Section: Methodsmentioning

confidence: 95%

“…[38,39] In particular, electrochemical oxidative selenenylation of alkyne or alkene using diselenides has been successfully demonstrated. [40,41] In 2018, Lei and co-workers demonstrate the electrochemical oxidative alkoxysulfonylation of alkenes by employing sulfonyl hydrazides and alcohols. [42] Herein, we reported the first electrochemical oxidative selenosulfonylation of alkynes using sulfonyl hydrazine and β-ketosulfones of alkenes by employing sulfonyl hydrazides (Scheme 1c).…”

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confidence: 99%

Electrochemical Oxidation‐induced Difunctionalization of Alkynes and Alkenes with Sulfonyl Hydrazides: Facile Access to β‐Selenovinyl Sulfones and β‐Ketosulfones

Kong

Chen

et al. 2020

Asian J Org Chem

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We report here in an efficient electrochemical oxidative selenosulfonylation of alkynes and oxysulfonylation of alkenes without use of metal catalysts. This method provides a practical access to a wide range of β-(seleno) vinyl sulfones and β-keto sulfones. These reactions can tolerate various functional groups and be easily scaled-up. Organosulfur compounds are frequently found in pharmaceuticals and biologically active natural products, and they are also crucial synthetic building blocks. [1-4] In particular, selenovinyl sulfones and β-ketosulfones are valuable synthetic intermediates and have a wide range of biological and pharmacological activities. [2,5-9] β-(Seleno)vinyl sulfones, which consist of vinyl selenide and vinyl sulfone units, [10-13] could be readily converted to several other useful products. [14-17] Therefore, a plethora of synthetic strategies have been developed for the synthesis of vinyl selenides. In 1983, Back et al. first used azobisisobutyronitrile (AIBN) as a free radical initiator to promote the cleavage of the preprepared PhSeSO 2 Ph reagent to construct β-(seleno)vinyl sulfone compounds. [18] In recent years, Li and Liu group reported that the multicomponent reaction of benzenesulfonyl hydrazide, diselenide, and alkyne could successfully afford β-(seleno)vinyl sulfone compounds under mild conditions through difunctionalization of the alkyne (Scheme 1a), [19-21] Recently, a four-component reaction has been developed for the preparation of a broad range of β-(seleno)vinyl sulfones with high levels of regioselectivity and stereoselectivity through sulfur dioxide insertion utilizing DABSO (Scheme 1a). [22] β-K etosulfones are widely used for the synthesis of organic functional materials and pharmaceuticals. [3] Consequently, considerable effort has been devoted to developing efficient strategies for their synthesis and functionalization [a

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“…In recent years, organic electrochemical synthesis has been widely considered as a sustainable, benign, and eco‐friendly synthetic tool that can realize the oxidation reaction through electron transfer and can be used to replace traditional oxidizing additives. This strategy has also been applied by Lei to achieve the electrochemical synthesis of seleno dihydrofurans and oxazolines [19] . Inspired by these studies and our previous research on electrosynthesis, [20–24] we conducted an electrochemical cyclization reaction between N ‐arylacrylamides and diselenides to obtain seleno oxindole products.…”

Section: Figurementioning

confidence: 99%

“…This strategy has also been applied by Lei to achieve the electrochemical synthesis of seleno dihydrofurans and oxazolines. [19] Inspired by these studies and our previous research on electrosynthesis, [20][21][22][23][24] we conducted an electrochemical cyclization reaction between N-arylacrylamides and diselenides to obtain seleno oxindole products. These products belong to a new class of compounds with better anticancer activity than compared with traditional oxindole derivatives and organic selenides.…”

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confidence: 99%

Synthesis of Seleno Oxindoles via Electrochemical Cyclization of N‐arylacrylamides with Diorganyl Diselenides

et al. 2020

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The tandem cyclization of acrylamide with diselenides facilitated by electrochemical oxidation was successfully developed. This strategy provided an environmentally friendly method for the construction of C−Se bond. A series of seleno oxindoles with pharmacological activity were obtained by using this well‐designed tandem cyclization strategy. The in vitro antitumor activity of the compounds was also screened through MTT assay. Results showed that the seleno oxindoles exhibited better antitumor activity than other oxindole derivatives.

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Electrochemical oxidative cyclization of olefinic carbonyls with diselenides

Abstract: The tandem cyclization of olefinic carbonyls with easily accessible diselenides facilitated by electrochemical oxidation has been successfully developed, which provides an environmentally friendly method for the construction of C–Se and C–O bonds simultaneously.

Cited by 83 publications

References 72 publications

Electrochemical Chalcogenation of β,γ‐Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines

Electrochemical Chalcogenation of β,γ‐Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines

Electrochemical Oxidation‐induced Difunctionalization of Alkynes and Alkenes with Sulfonyl Hydrazides: Facile Access to β‐Selenovinyl Sulfones and β‐Ketosulfones

Synthesis of Seleno Oxindoles via Electrochemical Cyclization of N‐arylacrylamides with Diorganyl Diselenides

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