Recent progress in the electrochemical selenofunctionalization of alkenes and alkynes

Green Chemistry, Год журнала: 2023, Номер 25(19), С. 7485 - 7507

Опубликована: Янв. 1, 2023

The recent advances on the electrochemical selenofunctionalization of unsaturated C–C bonds were comprehensively summarized in this review.

Язык: Английский

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Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(2), С. 597 - 630

Опубликована: Ноя. 23, 2023

This review highlights the recent progress in electrochemical difunctionalization of alkenes and alkynes involving C–S/Se bond formation to access organochalcogen frameworks.

Язык: Английский

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Electrophotocatalysis Versus Indirect Electrolysis: Electrochemical Selenocyclization of 3‐Aza‐1,5‐dienes Facilitated by Energy Transfer, Direct Photolysis or N‐Hydroxyphthalimide

Chemistry - A European Journal, Год журнала: 2024, Номер 30(36)

Опубликована: Апрель 23, 2024

Three hybrid electrochemical protocols, which involve the energy transfer, direct photolysis and N-hydroxyphthalimide catalyst, respectively, are presented for selenylation/cyclization of fragile substrates 3-aza-1,5-dienes with diorganyl diselenides to afford 3-selenomethyl-4-pyrrolin-2-ones. The two electrophotocatalytic reactions indirect electrolysis one both regioselective external-oxidant- transition-metal-free, associated a broad substrate scope high Se-economy, all three methods amenable gram-scale syntheses, late-stage functionalizations, sunlight-induced experiments all-solar-driven syntheses.

Язык: Английский

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A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 2500 - 2566

Опубликована: Окт. 9, 2024

With the resurgence of electrosynthesis in organic chemistry, there is a significant increase number routes available for late-stage functionalization (LSF) drugs. Electrosynthetic methods, which obviate need hazardous chemical oxidants or reductants, offer unprecedented control reactions through continuous variation applied potential and possibility combination with photochemical processes. This capability substantial advantage performing electrochemical photoelectrochemical LSF. Ultimately, these protocols are poised to become vital component medicinal chemist's toolkit. In this review, we discuss that have been demonstrated be applicable LSF pharmaceutical drugs, their derivatives, natural substrates. We present analyze representative examples illustrate electrochemistry photoelectrochemistry valuable molecular scaffolds.

Язык: Английский

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Electrochemical synthesis of selenyl imidazo[2,1-b]thiazinones via three-component reactions

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5813 - 5819

Опубликована: Янв. 1, 2024

In this paper, we have developed an efficient strategy for the concise synthesis of diverse selenyl imidazo[2,1- b ]thiazinones via electrochemical oxidative three-component tandem reactions in absence transition metals, and oxidants.

Язык: Английский

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Recent Progress on the Electro-Organic Synthesis for the 1,2-Difunctionalization of Alkenes

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер 23(10), С. 2323 - 2357

Опубликована: Янв. 1, 2025

In recent years, significant achievements have been made in the field of electroorganic chemistry regarding difunctionalization alkenes. Researchers developed innovative strategies utilizing unique reactivity electrochemical processes to synthesize complex molecules with high regioselectivity and stereoselectivity. This technology is widely applied total synthesis natural products pharmaceutical industry. article reviews research progress alkenes through three different radical-mediated pathways over past five years. It includes discussions on 1,2-stereoselective non-diastereoselective reactions, rearrangements, intramolecular migrations, cyclization processes. The summary emphasizes electrode designs, reaction mechanisms, integration other emerging technologies, highlighting potential this method modern organic chemistry. Additionally, it aims address current challenges propose possible solutions, providing a promising direction for electrochemically mediated reactions

Язык: Английский

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Intramolecular Acyl-Migration for Acyloxyselenenylation of Alkenes Promoted by Oxone

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 8, 2025

A novel green methodology for the Oxone-mediated oxidative addition of alkenes via intramolecular acyl migration has been developed. This transformation utilizes N-acyl-N-sulfonyl allylamines and diselenides as starting materials, with Oxone serving oxidant water a partial oxygen source. The protocol enables synthesis series β-acyloxy-γ-selenyl sulfonamides high to excellent yields demonstrates broad substrate scope. Notably, yield was maintained in gram-scale experiments, highlighting scalability this method. Through comprehensive control we have elucidated reaction mechanism, which involves rapid radical generation, predominant cationic pathway, migration. study presents an efficient environmentally benign approach valuable sulfonamides.

Язык: Английский

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Electrochemical Synthesis of α-Thiocyanated/Methoxylated Ketones Using Enol Acetates

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16122 - 16131

Опубликована: Ноя. 14, 2023

We have developed the synthesis of α-substituted ketone compounds with enol acetates in an electrochemical way. By using cheap NH4SCN and MeOH as radical sources, a series valuable α-thiocyanates/methoxy ketones were synthesized under mild electrolysis conditions acceptable yields diverse functional group compatibility. Additionally, scale-up experiment synthetic transformations reveal potential applications organic synthesis.

Язык: Английский

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Calcium(II)-Mediated Three-Component Selenofunctionalization of Alkenes under Mild Conditions

Organic Letters, Год журнала: 2023, Номер 25(45), С. 8095 - 8099

Опубликована: Ноя. 8, 2023

A mild and general protocol involving amnio- oxyselenation of diverse alkenes for the efficient synthesis organo-Se compounds is achieved via an environmentally benign calcium-catalyzed three-component reaction. This selenofunctionalization reaction exhibits excellent substrate/functional group tolerance high levels chemo- regioselectivity. Its utility was exemplified in late-stage functionalization even aggregation-induced emission luminogen labeling compounds.

Язык: Английский

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Calcium(II)-Mediated Three-Component Selenylation of gem-Difluoroalkenes: Access to α,α-Difluoroalkyl-β-selenides

Organic Letters, Год журнала: 2024, Номер 26(29), С. 6274 - 6278

Опубликована: Июль 15, 2024

A calcium-mediated three-component selenylation of gem-difluoroalkenes using alcohols as nucleophiles and N-(phenylseleno)phthalimide the agent has been developed for efficient synthesis various α,α-difluoroalkyl-β-selenides. This reaction exhibits broad substrate functional group tolerance, along with high levels chemo- regioselectivity. Additionally, synthetic utility transformation in late-stage functionalization drug molecules was demonstrated.

Язык: Английский

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