Visible-Light-Induced Glycosylation/Annulation of 2-Isocyanobiaryls and Glycosyl NHP Esters to Access Nonclassical Heteroaryl C-Glycosides

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

Опубликована: Янв. 13, 2025

A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple system, high diastereoselectivity, good functional group tolerance. In contrast to traditional strategies, this innovative approach circumvents need temperature, transition metal, photocatalyst, offering environmentally friendly efficient protocol.

Язык: Английский

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NHC-Catalyzed Tandem Reaction: A Strategy for the Synthesis of 2-Pyrrolidinone-Functionalized Phenanthridines

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16556 - 16565

Опубликована: Ноя. 16, 2023

Herein, an N-heterocyclic carbene (NHC)-catalyzed tandem cyclization/addition/cyclization reaction of 2-isocyanobiaryls and α-bromo-N-cinnamylamides for the synthesis 2-pyrrolidinone-functionalized phenanthridines is developed. This protocol features a radical cascade process, broad substrate scope, good functional group compatibility under metal- oxidant-free conditions.

Язык: Английский

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Visible-Light-Mediated Annulation/Thiolation of 2-Isocyanobiaryls with Disulfides to Organoylthiophenanthridines Derivatives

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 17322 - 17329

Опубликована: Дек. 4, 2023

A visible-light-induced annulation/thiolation of 2-isocyanobiaryls with dialkyl(aryl)disulfides has been established, delivering a sustainable and atom-economic route to 6-organoylthiophenanthridines wild functional group tolerance good excellent yields under oxidant-, base-, transition-metal-free conditions.

Язык: Английский

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Electro‐oxidative Methylation of 2‐Isocyanobiaryls Using N,N‐dimethylformamide (DMF) as Carbon Source: Synthesis of 6‐Methylphenanthridines

Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(9)

Опубликована: Март 16, 2024

A benign electrochemical method to access 6-methylphenanthridines from 2-isocyanobiaryls using N,N-dimethylformamide (DMF) as a methyl source is reported. The protocol operates at ambient temperature without the need for harmful methylating reagents. Mechanistic studies suggested that DMF delivered methylene synthon, followed by reduction cathode and tautomerization. offers environmental benefits avoiding metal-based reagents harsh conditions.

Язык: Английский

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Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Сен. 5, 2024

Abstract Fluoroalkylation serves as a pivotal strategy for chemists to precisely alter the properties of small molecules. Among established fluoroalkylation protocols, sulfone and sulfinate reagents stand out versatile tools these reactions, particularly in mono-, di-, trifluoromethylations. Their versatility lies offering multiple pathways, encompassing electrophilic, nucleophilic, well radical mechanisms, thus providing diverse routes controlled molecular modifications through variety very exciting mechanistic paths. 1 Introduction 2 Monofluoromethylation Strategies 2.1 Fluorobis(phenylsulfonyl)methane (FBSM) 2.2 2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide (FBDT) 2.3 Benzothiazole-SO2CH2F, NaSO2CH2F, ClSO2CH2F 2.4 PhSO2CH2F 3 Difluoromethylation 3.1 PhSO2CF2H 3.2 Benzothiazole-SO2CF2H 3.3 2-PyrSO2CF2H 3.4 NaSO2CF2H 4 Trifluoromethylation 4.1 PhSO2CF3 4.2 2-PyrSO2CF3 4.3 Benzothiazole-SO2CF3 4.4 NaSO2CF3 4.4.1 Electrochemical Approaches 4.4.2 Photochemical 4.4.3 Other Noteworthy 5 Conclusion

Язык: Английский

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Electrochemical trifluoroalkylation/annulation for the synthesis of CF₃-functionalized tetrahydroquinolines and dihydroquinolinones

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(42), С. 8579 - 8583

Опубликована: Янв. 1, 2023

Tuning the electronic structure of protecting groups on nitrogen atom substrates has emerged as an effective strategy to achieve tandem trifluoromethylation/C(sp2)-H annulation using Langlois' reagent CF3 source for electrochemical synthesis functionalized tetrahydroquinolines and dihydroquinolinones.

Язык: Английский

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Photoredox-catalyzed addition of isocyanides with boracene-based alkylborate: Construction of 6-alkylphenanthridine

Tetrahedron Letters, Год журнала: 2023, Номер 134, С. 154881 - 154881

Опубликована: Дек. 9, 2023

Язык: Английский

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Concise Synthesis of 2,4-Bis(Fluoroalkyl)Quinoline Derivatives from Arylamines

Опубликована: Янв. 1, 2024

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Язык: Английский

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Concise synthesis of 2,4-bis(fluoroalkyl)quinoline derivatives from arylamines

Tetrahedron, Год журнала: 2024, Номер 162, С. 134046 - 134046

Опубликована: Май 24, 2024

Язык: Английский

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