Electrochemical Organoselenium Catalysis for the Selective Activation of Alkynes: Easy Access to Carbonyl-pyrroles/oxazoles from <i>N</i>-Propargyl Enamines/Amides

Baidya, Mrinmay; Dutta, Jhilik; Sarkar, Suman De

doi:10.1021/acs.orglett.3c01355

Cited by 24 publications

(7 citation statements)

References 50 publications

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“…The activation of alkyne moiety 18”′ aa by PhSe + promoted to further cyclization with heteroatoms (N/O) to form a species 18“′ ab which subsequently oxidized three times in the presence of water to form desired product 19′′′ . N ‐propergylthioamides can have alternate to form thiazole synthesis under electrochemical conditions but the described methodology is not included for this studies [49d] …”

Section: Carbonyl Functionalizationmentioning

confidence: 99%

Progress in Electrochemically Empowered C−O Bond Formation: Unveiling the Pathway of Efficient Green Synthesis

Ghosh,

Samal,

Parida

et al. 2024

Chemistry An Asian Journal

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(C‐X) bonds (X= C, N, O) are the main backbone for making different skeleton in the organic synthetic transformations. Among all the sustainable techniques, electro‐organic synthesis for C‐X bond formation is the advanced tool as it offers a greener and more cost‐effective approach to chemical reactions by utilizing electrons as reagents. In this review, we want to explore the recent advancements in electrochemical C‐O bond formation. The electrochemically driven C‐O bond formation represents an emerging and exciting area of research. In this context, electrochemical techniques offers numerous advantages, including higher yields, cost‐efficient production, and simplified work‐up procedures. This method enables the continuous and consistent formation of C‐O bonds in molecules, significantly enhancing overall reaction yields. Furthermore, both intramolecular and intermolecular C‐O bond forming reaction provided valuable products of O‐containing acyclic/cyclic analogue. Hence, carbonyl (C=O), ether (‐O‐), and ester (–COOR) functionalization in both cyclic/acyclic analogues have been prepared continuously via this innovative pathway. In this context, we want to discuss one‐decade electrochemical synthetic pathways of various C‐O bond contains functional group in chronological manner. This review focused on all the synthetic aspects including mechanistic path and has also mentioned overall critical finding regarding the C‐O bond formation via electrochemical pathways.

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Section: Carbonyl Functionalizationmentioning

confidence: 99%

Progress in Electrochemically Empowered C−O Bond Formation: Unveiling the Pathway of Efficient Green Synthesis

Ghosh,

Samal,

Parida

et al. 2024

Chemistry An Asian Journal

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“…Recently (2023), Sarkar and co-workers [ 39 ] described the synthesis of carbonyl-pyrroles 26 or 27 or -oxazole 5 using diphenyl diselenide A as an electrocatalyst, which activates the alkyne portion of the N -propargyl derivatives (enamines 25 or amides 4 ). This is a sustainable redox process that promotes an intramolecular electro-oxidative addition reaction activated by a cationic phenyl selenium species ( Scheme 26 ).…”

Section: Application Of Diorganyl Diselenide As a Catalystmentioning

confidence: 99%

Recent Advances in the Use of Diorganyl Diselenides as Versatile Catalysts

da Costa,

Blödorn,

Barcellos

et al. 2023

Molecules

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The importance of organoselenium compounds has been increasing in synthetic chemistry. These reagents are well-known as electrophiles and nucleophiles in many organic transformations, and in recent years, their functionality as catalysts has also been largely explored. The interest in organoselenium-based catalysts is due to their high efficacy, mild reaction conditions, strong functional compatibility, and great selectivity. Allied to organoselenium catalysts, the use of inorganic and organic oxidants that act by regenerating the catalytic species for the reaction pathway is common. Here, we provide a comprehensive review of the last five years of organic transformations promoted by diorganyl diselenide as a selenium-based catalyst. This report is divided into four sections: (1) cyclisation reactions, (2) addition reactions and oxidative functionalisation, (3) oxidation and reduction reactions, and (4) reactions involving phosphorus-containing starting materials.

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“…[26][27][28][29][30][31][32] Construction of CÀ Se bonds through an electrochemical strategy has garnered increasing interest. [33][34][35][36][37][38][39][40][41][42][43][44][45] The electrochemical strategy involves the reduction of diselenides at the cathode to form an anion radical intermediate, which is further transformed into selenium radicals and anions. The selenium anions can be subsequently oxidized to selenium radicals at the anode.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Stereoselective Synthesis of (Z)‐Allyl Aryl Selenides and Sulfides from Baylis‐Hillman Acetates

Sun,

Xia,

et al. 2024

Adv Synth Catal

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This research presents a method for the oxidative selenylation and thiolylation of Morita–Baylis–Hillman adducts through constant‐current electrolysis in an undivided cell at room temperature. The reaction enables direct production of trisubstituted (<i>Z</i>)‐allyl aryl selenides and sulfides with yields of 27–98%. A wide variety of different functionalities are well tolerated under this reaction condition, contributing to the substrate scope and applicability. Additionally, this strategy is amenable to gram‐scale synthesis and several synthetic transformations are accomplished for the construction of other allyl‐selenide derivatives. Both control experiments and mechanistic studies indicate a radical or an ionic addition pathway for this electrochemical transformation.

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Electrochemical Organoselenium Catalysis for the Selective Activation of Alkynes: Easy Access to Carbonyl-pyrroles/oxazoles from N-Propargyl Enamines/Amides

Cited by 24 publications

References 50 publications

Progress in Electrochemically Empowered C−O Bond Formation: Unveiling the Pathway of Efficient Green Synthesis

Progress in Electrochemically Empowered C−O Bond Formation: Unveiling the Pathway of Efficient Green Synthesis

Recent Advances in the Use of Diorganyl Diselenides as Versatile Catalysts

Electrochemical Stereoselective Synthesis of (Z)‐Allyl Aryl Selenides and Sulfides from Baylis‐Hillman Acetates

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