Electrochemical Selenylation of Alkynyl Aryl Ketones: Efficient Synthesis of 3‐Selenylated Chromones under Catalyst‐ and Chemical‐Oxidant‐Free Conditions

Cen, Kaili; Wei, Jiahao; Liu, Yuan; Tan, Zhixuan; Wang, Xinye; Wang, Dahan; He, Wei‐Min; Cai, Jinhui

doi:10.1002/ejoc.202300968

Cited by 8 publications

References 42 publications

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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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Recent Developments in Selenylation of Alkynes

Xu,

Huang,

et al. 2024

Adv Synth Catal

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Electrochemical Synthesis of 4‐Selenylated Oxazolones via Oxyselenylation of Ynamides

Cai,

Cen,

et al. 2024

Adv Synth Catal

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Electrosynthesis of selenylated‐oxazolone derivatives via cascade selenylation/cyclization of ynamides was disclosed. A series of diaryl diselenides, dialkyl diselenides, and heteroaryl‐substituted ynamides was tolerated in this protocol and delivered 4‐selenyloxazolones in 28‐83% yield. The scale‐up reaction and the oxidation of selenylated‐oxazolones was performed to showcase the practicability of this method. Furthermore, mechanistic experiments indicated that a cationic pathway instead of aradical pathway was probably involved.

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Selenylation of N‐(P‐Methoxyaryl)Propiolamides via CuBr₂ Catalysis: Synthesis of 3‐Selenospiro[4,5]Decatrienones via Ipso‐Cyclization

Cai,

Cen,

Lin

et al. 2024

ChemCatChem

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Herein, a method for the assembly of biologically valuable 3‐selenospiro[4,5]decatrienones through CuBr2‐catalyzed ispo‐cyclization of Se powder, boronic acids, and N‐(p‐methoxyaryl)propiolamides has been established. In this protocol, noble transition metal, prefunctionalized selenylation reagent, and strong chemical oxidant are not employed. This method feature wide substrate scope, good functional group tolerance, easy operation, and employing earth‐abundant metal as catalyst and green air as oxidant. Furthermore, several derivatizations of 3‐selenospiro[4,5]decatrienones are performed to showcase the practicability of our strategy.

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Electrochemical Selenylation of Alkynyl Aryl Ketones: Efficient Synthesis of 3‐Selenylated Chromones under Catalyst‐ and Chemical‐Oxidant‐Free Conditions

Cited by 8 publications

References 42 publications

Recent Developments in Selenylation of Alkynes

Recent Developments in Selenylation of Alkynes

Electrochemical Synthesis of 4‐Selenylated Oxazolones via Oxyselenylation of Ynamides

Selenylation of N‐(P‐Methoxyaryl)Propiolamides via CuBr₂ Catalysis: Synthesis of 3‐Selenospiro[4,5]Decatrienones via Ipso‐Cyclization

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Electrochemical Selenylation of Alkynyl Aryl Ketones: Efficient Synthesis of 3‐Selenylated Chromones under Catalyst‐ and Chemical‐Oxidant‐Free Conditions

Cited by 8 publications

References 42 publications

Recent Developments in Selenylation of Alkynes

Recent Developments in Selenylation of Alkynes

Electrochemical Synthesis of 4‐Selenylated Oxazolones via Oxyselenylation of Ynamides

Selenylation of N‐(P‐Methoxyaryl)Propiolamides via CuBr2 Catalysis: Synthesis of 3‐Selenospiro[4,5]Decatrienones via Ipso‐Cyclization

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Selenylation of N‐(P‐Methoxyaryl)Propiolamides via CuBr₂ Catalysis: Synthesis of 3‐Selenospiro[4,5]Decatrienones via Ipso‐Cyclization