The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 21, 2024
A visible-light-driven radical C-H methylation of
Language: Английский
ACS Sustainable Chemistry & Engineering, Journal Year: 2023, Volume and Issue: 11(35), P. 13142 - 13148
Published: Aug. 24, 2023
Benzothiazolines, with their versatile nature, serve as fundamental building blocks for the synthesis of significant biological compounds. However, methods preparation benzothiazolines from readily available starting materials are limited. An efficient benzothiazoline via photoredox-catalyzed dearomatization benzothiazole derivatives has been achieved at room temperature. This catalysis proceeds a ligand to metal charge transfer process, and FeCl3 plays dual role an indirect HAT reagent reducing agent. methodology can be conveniently scaled up, most alkylated products purified without chromatography. In addition, this process exhibited advantages low cost, high reaction efficiency, mild conditions.
Language: Английский
Citations
11
Green Chemistry, Journal Year: 2024, Volume and Issue: 26(14), P. 8161 - 8203
Published: Jan. 1, 2024
The strategic installation of the “magic methyl” group has become highly desirable for drug discovery. This review summarized recent photochemical and electrochemical strategies in installing methyl group.
Language: Английский
Citations
4
Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 365(2), P. 142 - 147
Published: Dec. 17, 2022
Abstract A photocatalyzed metal‐free method for benzylic C(sp 3 )−H bond oxidation has been developed. Achieved under the mild conditions, a variety of methylarenes and benzyl derivatives could be converted into corresponding carboxylic acids ketones, isolated yields 31–98% are obtained. The mechanistic investigations showed that chlorine radical generated via direct single electron transfer (SET) between chloride anion excited heteroarene light irradiation, which used as hydrogen atom agent to facilitate oxygenation. merits this catalytic system further demonstrated by degradation plastic form benzoic acids. magnified image
Language: Английский
Citations
18
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(4), P. 612 - 617
Published: Jan. 26, 2023
Abstract A mild visible‐light induced 4CzIPN/H + photoredox system has been developed that enables hydroxyketones serving as a carbon radical precursor via formal C−O bond cleavage. This process was successfully exploited in the coupling/cyclization reaction of N‐arylacrylamides and thereby provided viable access to acyl oxindoles. protocol features advantages including no need for any metal catalyst additive, high yielding, broad substrate scope, gram scalability, release H 2 O sole byproduct. magnified image
Language: Английский
Citations
10
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 27, 2025
In this work, we developed a general catalytic strategy that allows Minisci C-H alkylation of variety heterocycles using unactivated alkyl halide as an radical source under visible light photocatalysis. Mild reaction conditions, employing 4CzIPN organophotocatalyst and aerial oxygen green terminal oxidant, broad scope, good functional group tolerance, late-stage bioactive pharmaceutically relevant molecules are advantages the protocol. Preliminary mechanistic studies indicate involvement α-amino further our conditions.
Language: Английский
Citations
0
Coordination Chemistry Reviews, Journal Year: 2025, Volume and Issue: 537, P. 216677 - 216677
Published: April 14, 2025
Language: Английский
Citations
0
Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(72)
Published: Oct. 6, 2023
Direct C-H methylation is a highly valuable approach for introducing methyl groups into organic molecules, particularly in pharmaceutical chemistry. Among the various methodologies available, photo-induced stands out as an exceptional choice due to its mild reaction conditions, energy efficiency, and compatibility with functional groups. This article offers comprehensive review of photochemical strategies employed direct selective C(sp3 )-H, C(sp2 C(sp)-H bonds molecules. The discussed encompass transition-metal-based photocatalysis, organophotocatalysis, well other metal-free approaches, including electron donor-acceptor (EDA)-enabled transformations. Importantly, wide range easily accessible agents such tert-butyl peroxide, methanol, DMSO, ether, TsOMe, N-(acetoxy)phthalimide, acetic acid, halides, even methane can serve effective methylating reagents modifying diverse targets. These advancements are anticipated drive further progress fields synthesis, development, opening up exciting avenues creating novel molecules discovering new drug compounds.
Language: Английский
Citations
9
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3629 - 3634
Published: Feb. 16, 2024
The visible-light-promoted deoxygenative radical heteroarylation of alcohols was achieved in the absence any external photosensitizers. processes occur through generation xanthate salts from alcohols, followed by SET and fragmentation, delivering alkyl radicals to react with heteroaryl sulfones. This method is amenable for a wide range good functional group tolerance, providing practical strategy alkylation benzo-heteroaromatics. Mechanism studies indicate that direct visible-light excitation anions subsequent initiate reactions.
Language: Английский
Citations
3
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(18), P. 4709 - 4717
Published: Jan. 1, 2023
Difluorinated compounds are important structural motifs in organic synthesis and medicinal chemistry because fluoride can modulate the properties of various molecules.
Language: Английский
Citations
7
Green Chemistry, Journal Year: 2023, Volume and Issue: 25(21), P. 8500 - 8504
Published: Jan. 1, 2023
This work presents a scalable and mild strategy for aliphatic C–H arylation with heteroarenes under metal-free, photocatalyst-free strong oxidant-free conditions.
Language: Английский
Citations
7