Metal-free electrochemical oxidative intramolecular cyclization of<i>N</i>-propargylbenzamides: facile access to oxazole ketals

Zhang, Huaxin; Xiong, Y.; Luo, Mu‐Jia; Yang, Ruchun; Bai, Jiang; Song, Xian‐Rong; Song, Xian‐Rong

doi:10.1039/d3qo00662j

Cited by 8 publications

(2 citation statements)

References 59 publications

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“…An electrochemical reaction of N -propargylbenzamides for the synthesis of oxazole ketals was developed by the Xiao group in 2023. The reaction of N -propargylbenzamides 517 and n -Bu 4 NPF 6 in an undivided cell with graphite rod anode and platinum plate cathode for 5 h produced oxazole ketals 518 in moderate to good yields ( Scheme 103 ) [ 126 ]. In this reaction, anions generated from the deprotonation of 517 with MeO – undergo anodic oxidation to give N -centered radicals 519 which have O -centered radicals 520 as the resonance structures.…”

Section: Second Functionalization With Other Forms Of Y (Y ...mentioning

confidence: 99%

Radical Cyclization-Initiated Difunctionalization Reactions of Alkenes and Alkynes

Zhi,

Ma,

Zhang

2024

Molecules

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Radical reactions are powerful in the synthesis of diverse molecular scaffolds bearing functional groups. In previous review articles, we have presented 1,2-difunctionalizations, remote 1,3-, 1,4-, 1,5-, 1,6- and 1,7-difunctionalizations, and addition followed by cyclization reactions. Presented in this paper is radical cyclization followed by the second functionalization reaction. The second functionalization could be realized by atom transfer reactions, radical or transition metal-assisted coupling reactions, and reactions with neutral molecules, cationic and anionic species.

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Section: Second Functionalization With Other Forms Of Y (Y ...mentioning

confidence: 99%

Radical Cyclization-Initiated Difunctionalization Reactions of Alkenes and Alkynes

Zhi,

Ma,

Zhang

2024

Molecules

View full text Add to dashboard Cite

show abstract

“…An electrochemical reaction of N-propargylbenzamides for the synthesis of oxazole ketals was developed by the Xiao group in 2023. The reaction of N-propargylbenzamides 517 and n-Bu4NPF6 in an undivided cell with graphite rod anode and platinum plate cathode for 5 h produced oxazole ketals 518 in moderate to good yields (Scheme 103) [126]. In this reaction, anions generated from the deprotonation of 517 with MeOundergo anodic oxidation to give N-centered radicals 519 which have O-centered radicals 520 as the resonance structures.…”

Section: Second Functionalization With Other Forms Of Y (Y •+ Y + A...mentioning

confidence: 99%

Radical Cyclization-initiated Difunctionalization Reactions of Alkenes and Alkynes

Zhi,

Ma,

Zhang

2024

Preprint

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Radical reactions are powerful in the synthesis of diverse molecular scaffolds bearing functional groups. In pervious review articles, we have presented 1,2-difunctionalizations, remote 1,3-, 1,4-, 1,5-, 1,6- and 1,7-difunctionalizations, and addition followed by cyclization reactions. Presents in this paper are radical cyclization followed by the second functionalization reactions. The second functionalization could be realized by atom transfer reactions, radical or transition metal-assisted coupling reactions, and reactions with neutral molecules, cationic and anionic species.

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Synthesis of Selenooxazoles through Electrochemical Oxidative Selenocyclization ofN‐Propargylamides

Zhang,

Xiong,

Song

et al. 2023

Adv Synth Catal

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An electrocatalytic approach for the bromide‐mediated selenocyclization of N‐propargylamides with diselenides is described, providing a synthetic route for the synthesis of various seleno‐oxazoles in 41–73% yields. The success of gram‐scale experiments demonstrate the potential value of this protocol in synthetic chemistry. Mechanistic investigations suggest that this selenocyclization protocol proceed through two possible pathways, including selenium cation and radical processes.

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Metal-free electrochemical oxidative intramolecular cyclization ofN-propargylbenzamides: facile access to oxazole ketals

Abstract: Here, an unprecedented and sustainable electrochemically driven oxidative 5-exo-dig radical cyclization of N-propargylbenzamides with alcohols is described, which providing a straightforward method to quickly deliver the structurally diverse oxazole ketals...

Cited by 8 publications

References 59 publications

Radical Cyclization-Initiated Difunctionalization Reactions of Alkenes and Alkynes

Radical Cyclization-Initiated Difunctionalization Reactions of Alkenes and Alkynes

Radical Cyclization-initiated Difunctionalization Reactions of Alkenes and Alkynes

Synthesis of Selenooxazoles through Electrochemical Oxidative Selenocyclization ofN‐Propargylamides

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