Light-induced homolysis of copper(ii)-complexes – a perspective for photocatalysis

Chemical Science, Год журнала: 2023, Номер 14(17), С. 4449 - 4462

Опубликована: Янв. 1, 2023

A new kid on the block: Cu( ii ) offers unique possibilities in photocatalysis for generating and stabilizing radicals to promote challenging synthetic transformations.

Язык: Английский

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Preparation of Sulfilimines by Sulfur-Alkylation of N-Acyl Sulfenamides with Alkyl Halides

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 7607 - 7614

Опубликована: Май 24, 2023

Sulfur alkylation of N-acyl sulfenamides with alkyl halides provides sulfilimines in 47% to 98% yields. A broad scope was established a variety aryl and sulfenamides, including for different groups. Alkyl steric electronic properties were effective inputs, methyl, primary, secondary, benzyl, propargyl halides. proof-of-concept asymmetric phase-transfer also demonstrated. sulfilimine product readily converted an free sulfoximine, which represent important motifs medicinal chemistry.

Язык: Английский

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Towards a more Sustainable Photocatalysis using Copper and Iron

Current Opinion in Green and Sustainable Chemistry, Год журнала: 2025, Номер unknown, С. 100998 - 100998

Опубликована: Янв. 1, 2025

Язык: Английский

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Iron-Catalyzed Photochemical Synthesis of Sulfinamides from Aliphatic Hydrocarbons and Sulfinylamines

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3703 - 3708

Опубликована: Апрель 26, 2024

An iron-catalyzed photochemical sulfinamidation of hydrocarbons with

Язык: Английский

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Photoinduced Ligand-to-Metal Charge Transfer in Base-Metal Catalysis

Synthesis, Год журнала: 2023, Номер 56(13), С. 1967 - 1978

Опубликована: Ноя. 21, 2023

Abstract The absorption of light by photosensitizers has been shown to offer novel reactive pathways through electronic excited state intermediates, complementing ground-state mechanisms. Such strategies have applied in both photocatalysis and photoredox catalysis, driven generating intermediates from their long-lived states. One developing area is photoinduced ligand-to-metal charge transfer (LMCT) which coordination a ligand metal center subsequent excitation with results the formation radical reduced center. This mini review concerns foundations recent developments on transition-metal focusing organic transformations made possible this mechanism. 1 Introduction 2 Iron 3 Cobalt 4 Nickel 5 Copper 6 Future Outlook Conclusion

Язык: Английский

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Rhodium-Catalyzed Enantioselective N-Allylation of Sulfoximines

Organic Letters, Год журнала: 2023, Номер 25(16), С. 2756 - 2760

Опубликована: Апрель 14, 2023

The N-functionalization of free sulfoximines is an important approach to modifying their chemical and biological properties for downstream applications. Here, we report a rhodium-catalyzed N-allylation (═NH) with allenes under mild conditions. redox-neutral base-free process enables chemo- enantioselective γ-hydroamination gem-difluoroallenes. Synthetic applications sulfoximine products obtained thereof have been demonstrated.

Язык: Английский

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Electrochemical N‐Aroylation of Sulfoximines by Using Benzoyl Hydrazines with H₂ Generation

Chemistry - A European Journal, Год журнала: 2023, Номер 30(9)

Опубликована: Ноя. 22, 2023

Abstract Developed here is a robust electrochemical cross‐coupling reaction between aroyl hydrazine and NH ‐sulfoximine via concomitant cleavage formation of C(sp 2 )−N bonds with the evolution H N as innocuous by‐products. This sustainable protocol avoids use toxic reagents occurs at room temperature. The proceeds generation an sulfoximidoyl radical anodic oxidation under constant current electrolysis (CCE), affording ‐aroylated sulfoximine. strategy applied to late‐stage sulfoximidation L‐menthol, (−)‐borneol, D‐glucose, vitamin‐E derivatives, marketed drugs such probenecid, ibuprofen, flurbiprofen, ciprofibrate, sulindac. In addition, present methodology mild, high functional group tolerance broad substrate scope scalable.

Язык: Английский

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Light‐Induced Vicinal Dichlorination of Alkenes Using FeCl₃ as the Dichlorination Reagent

ChemistrySelect, Год журнала: 2024, Номер 9(6)

Опубликована: Фев. 7, 2024

Abstract We report a ligand‐to‐metal charge‐transfer (LMCT) process that used ferric (III) chloride as efficient chlorination reagent to mediate the vicinal dichlorination of alkenes. Under 420 nm LED light, easily available and safe could facilitate various alkenes transform 1,2‐dichloride compounds with good excellent yields (19 examples). The strategy showed more economic protocol than CuCl 2 , provided significant reference for light‐Induced in industrial catalysis.

Язык: Английский

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Cu(ii) salts as terminal oxidants in visible-light photochemical oxidation reactions

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 22(1), С. 25 - 36

Опубликована: Ноя. 22, 2023

Photochemistry provides an important platform for the discovery of synthetically useful transformations. The development new oxidative photoreactions, however, has proven to be relatively challenging. importance identity terminal oxidant been underappreciated consideration in design these reactions. Many most common oxidants used ground-state catalytic methods are poorly compatible with one-electron oxidation state changes characteristic photoredox reactions and result hard-to-control deleterious side As alternative, Cu(II) salts have emerged as versatile photochemical that terrestrially abundant, cost-effective, readily changes. This review highlights recent reaction leverage combination activation substrates or use both active chromophore oxidant.

Язык: Английский

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Base-Promoted Synthesis of S-Arylisothiazolones via Intramolecular Dehydrative Cyclization of α-Keto-N-acylsulfoximines

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 778 - 783

Опубликована: Дек. 14, 2023

A base (Et3N)-promoted synthesis of 1,4-diarylisothiazolones from α-keto-N-acylsulfoximines has been achieved. The reaction proceeds via α-hydrogen abstraction sulfoximine, followed by an intramolecular nucleophilic attack at the keto carbonyl to form a tert-hydroxy isothiazolone intermediate. 1,4-substituted is obtained after dehydration E1cB path. This one-pot isothiazolinones broad substrate scope, high atom economy, and provides products with good yields. ΔELUMO–HOMO calculated using Gaussian 16 B3LYP/6-31G(d,p) level theory.

Язык: Английский

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