Benzylic C–H Oxidation: Recent Advances and Applications in Heterocyclic Synthesis DOI Creative Commons

Nonhlelo Majola,

Vineet Jeena

Molecules, Journal Year: 2024, Volume and Issue: 29(24), P. 6047 - 6047

Published: Dec. 22, 2024

Benzylic C–H oxidation to form carbonyl compounds, such as ketones, is a fundamental transformation in organic synthesis it allows for the preparation of versatile intermediates. In this review, we highlight aromatic ketones via catalytic, electrochemical, and photochemical alkylarenes using different catalysts oxidants past 5 years. Additionally, also discuss heterocyclic molecules benzylic key step. These methods can potentially be used medicinal, synthetic, inorganic chemistry.

Language: Английский

Solvent-free oxidation of benzylic C(sp3)–H bond over MA3Bi2Br9 perovskite photocatalyst by efficient singlet oxygen generation DOI
Lijuan Shen, Hao Kang,

Lixun Deng

et al.

Journal of Catalysis, Journal Year: 2024, Volume and Issue: 434, P. 115499 - 115499

Published: April 15, 2024

Language: Английский

Citations

14

Photochemical upcycling and recycling of plastics: achievements and future opportunities DOI Creative Commons
Olga G. Mountanea,

Elpida Skolia,

Christoforos G. Kokotos

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(15), P. 8528 - 8549

Published: Jan. 1, 2024

Recent developments in the photochemical upcycling and recycling of plastics.

Language: Английский

Citations

12

C(sp<sup>3</sup>)‐H Functionalization Using Chlorine Radicals DOI
Masoud Sadeghi

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(13), P. 2898 - 2918

Published: May 18, 2024

Abstract Converting any desired C−H bond to the intended C−Z in a given organic molecule could be final peak of functionalization methodology. Among three types bonds, ubiquitous C( sp 3 )−H has gained particular attention, especially last two decades. There are different ways transform bonds into bonds. The use chlorine radicals is one these methods with promising future. literature review shows that sources have been used for chlorine, including chloride ions (HCl or salts), coordinated chlorides (transition metal complexes), and (organochlorine compounds). However, HCl FeCl most attention among sources. major convert from radicals: 1) oxidation hydrogen salts, 2) photolysis chloride, 3) transition insertion C−Cl This summarizes published research papers on functionalization. Therefore, chlorination reactions which do not play direct role cleavage within scope this review.

Language: Английский

Citations

8

Iron-Catalyzed Photoredox Intermolecular Dearomatization of Benzothiazoles with Alkanes DOI
Ning Xu, Xiaoqing Peng, Zhi Chen

et al.

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

Aerobic Benzylic C(sp3)–H Bond Oxygenations Catalyzed by NBS under Visible Light Irradiation DOI

Taiqiang Ye,

Yuzheng Li,

Yanni Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 534 - 540

Published: Dec. 22, 2023

An efficient photocatalytic oxidation of benzylic C(sp3)–H bonds to ketones, esters, and amides has been developed using NBS as a metal-free photocatalyst O2 an oxidant. A variety synthetically biologically valuable compounds are assembled in moderate excellent yields. The synthetic utility this approach demonstrated by gram-scale experiments. possible free radical mechanism was proposed rationalize the reaction procedure.

Language: Английский

Citations

10

Visible-Light-Driven Oxidation of Benzylic C—H Bonds Enabled by Anthraquinone in Water DOI
Chen Duan, Siyu Shen, Yuqi Zhao

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(4), P. 1352 - 1352

Published: Jan. 1, 2025

Language: Английский

Citations

0

Photoinduced regioselective difluorination of secondary inert C(sp3)–H bonds in sulfonamides via 1,5-hydrogen-atom transfer DOI

Zhi Chen,

Wenkai Zhu,

Chaodong Wang

et al.

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

Photo- and electro-induced perfluoroalkylation/cyclization of o-hydroxyaryl enaminones: Synthesis of perfluoroalkyl chromones DOI Creative Commons

Shengjie Song,

Wenjian Wang,

Jun Sun

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: March 1, 2024

A practical, metal-, and additive-free strategy for photo- electro-induced perfluoroalkylation/cyclization of o-hydroxyaryl enaminones with sodium perfluoroalkanesulfinates under mild conditions has been developed. Various fluoroalkyl chromones were efficiently assembled in moderate to good yields. The scalability this protocol the assembling diverse nitrogen-containing heterocycles from late-stage transformations greatly broaden practical applications developed protocol.

Language: Английский

Citations

2

Photocatalytic selective oxidation of toluene under encapsulated air conditions DOI

Jing Cui,

Kaikai Niu, Rong‐Zhen Zhang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(32), P. 4310 - 4313

Published: Jan. 1, 2024

We report herein a mild and practical photocatalytic selective oxidation of toluene under encapsulated air conditions low catalyst loading, while simultaneously accommodating broad applicability for various high value-added aromatic aldehydes.

Language: Английский

Citations

2

Enhanced C(sp3)–H Selective Oxidation Using Efficient Polyoxometalate-Based Metal–Organic Framework Photocatalysts Synergized with Ir Metalloligands and Polyoxometalates DOI
Jing Wang,

Luoning Li,

Yanan Liu

et al.

Chemistry of Materials, Journal Year: 2024, Volume and Issue: 36(22), P. 11150 - 11159

Published: Nov. 9, 2024

Achieving efficient selective visible light-induced oxidation of benzyl C(sp3)–H to more valuable double-bonded compounds holds significant promise for organic synthesis. In this work, we fabricated an example Ir metalloligand-modified POMOF crystalline material, CI-SiW, which is noteworthy as the first POM immobilized in a MOF via coordination bonding. Under excitation light (10 W, λ = 410 nm), CI-SiW can catalyze isochromane with turnover number and frequency 954 1740 h–1, respectively. Excitingly, displays best TOF compared previous photocatalysts under same conditions, realizing maximum yield minimum amount photocatalyst. Furthermore, had good cyclic structural stability, 90.4% was still obtained after three reaction cycles.

Language: Английский

Citations

2