Photoinduced Lignin C α −C β Bond Cleavage and Chemodivergent Functionalization via Iron Catalysis DOI

Yi Li,

Simeng Wu,

Yongqian Liu

и другие.

ChemSusChem, Год журнала: 2024, Номер unknown

Опубликована: Июль 22, 2024

Abstract The photocatalytic conversion of lignin into value‐added chemicals especially those functionalized molecules represent one the most important strategies for sustainable and environmental‐friendly development. Cleavage C−C bonds in under mild conditions refining useful is meaningful but challenging. Meanwhile, assembly diverse functional groups active fragments during depolymerization great Herein, using cheap iron catalysts visible light irradiation, highly selective efficient cleavage C α −C β bond realized via ligand‐to‐metal charge transfer (LMCT) hydrogen atom (HAT) processes. subsequent divergent functionalization generated fragment‐based radical intermediates enables an formation molecules. This method also effective native lignin, yielding two identified benzaldehyde monomers a total yield 8.7 wt %.

Язык: Английский

Recent advances in FeCl3-photocatalyzed organic reactions via hydrogen-atom transfer DOI
Xiaoya Yuan, Congcong Wang, Bing Yu

и другие.

Chinese Chemical Letters, Год журнала: 2024, Номер 35(9), С. 109517 - 109517

Опубликована: Янв. 21, 2024

Язык: Английский

Процитировано

38

The great strides of iron photosensitizers for contemporary organic photoredox catalysis: On our way to the holy grail? DOI
Felix Glaser,

Akin Aydogan,

Benjamin Elias

и другие.

Coordination Chemistry Reviews, Год журнала: 2023, Номер 500, С. 215522 - 215522

Опубликована: Ноя. 9, 2023

Язык: Английский

Процитировано

28

Photoinduced C−O Bond Formation through C−C Bond Cleavage of Alcohols by Suppressing Alcohol Oxidation DOI
Qiang Wu, Peng Hu

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(7), С. 1595 - 1605

Опубликована: Фев. 3, 2024

Abstract Herein, we present a photoinduced deconstructive alkoxyamination of alkyl alcohols catalyzed by iron salts. This transformation involves the initiation alkoxy radicals through chlorine radical‐induced radical formation, followed β ‐scission and trapping resulting carbon with 2,2,6,6‐tetramethylpiperidin‐1‐yl (TEMPO). reaction exhibits broad substrate scope (40 examples), including primary secondary that are prone to oxidation combination TEMPO iron. Mechanistic investigations have revealed enhanced coordination chloride ion center inhibits OH process, thereby enabling tolerance alcohols.

Язык: Английский

Процитировано

6

Synergistic use of photocatalysis and convergent paired electrolysis for nickel-catalyzed arylation of cyclic alcohols DOI

Zhao‐Ran Liu,

Xiaoyu Zhu,

Jianfeng Guo

и другие.

Science Bulletin, Год журнала: 2024, Номер 69(12), С. 1866 - 1874

Опубликована: Апрель 16, 2024

Язык: Английский

Процитировано

6

Demystifying the recent photochemical and electrochemical tricks on installing the magic methyl group: A comprehensive overview DOI

Feiyang Liao,

Zenghui Wei,

Yunhao Guan

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(14), С. 8161 - 8203

Опубликована: Янв. 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.

Язык: Английский

Процитировано

4

Deconstructive Cyanomethylation Enabled by Radical Cross‐Coupling through Multiple C−C Bond and C−H Bond Cleavage DOI

Changzhen Yin,

Wei Liu, Qiang Wu

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(7), С. 1072 - 1081

Опубликована: Март 17, 2023

Abstract Being in its infancy, radical cross‐coupling is highly efficient for C−C bond construction, though suffers from selectivity problems and limited reaction types. New methodologies to realize selectively are desired. Herein, an iron catalyzed deconstructive cyanomethylation of unstrained cyclic linear alcohols with acetonitrile has been developed through cross‐coupling. The unprecedented method enables a ring‐opening functionalization cyclohexanols produce α‐cyanomethyl ketones. Notably, the challenging involves twice single cleavage β‐scission alkoxyl intermediates, C( sp 3 )−H transformation via hydrogen atom transfer (HAT) procedures, resulting two carbon species that process form new )−C( ) selectively. α‐arylketo α‐aryl substituted tertiary can also be applied as substrates, leading terminal cyano‐functionalized products, ketone leaving fragment. Mechanistically, procedure generate chlorine in‐situ formed intermediate cycloalkyl hypochlorite was suggested. magnified image

Язык: Английский

Процитировано

9

Recent Development of Photoinduced Iron-Catalysis in Organic Synthesis DOI Open Access
Qian Dou, Taimin Wang, Lijing Fang

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(4), С. 1386 - 1386

Опубликована: Янв. 1, 2023

In recent years, the development and application of transition metal ruthenium or iridium complexes based photocatalysts have opened up a new research field for organic synthesis, which provides mild efficient strategies construction chemical bonds transformations.In order to enrich types photocatalysts, broaden scope photocatalysis, develop green sustainable chemistry, some low-cost easily available organometallic with copper iron were applied as recently.Iron-complexes feature non-toxicity, rich variety, unique property charge transfer from ligands metals, enable them show extraordinary capability in photocatalytic synthesis.According different reaction types, this review focuses on photoinduced iron-catalysis synthesis including C-H bond functionalization, C-C bifunctionalization alkenes, cross-coupling reaction, decarboxylative selective oxidation reduction.

Язык: Английский

Процитировано

9

Solvent-promoted photochemical carbonylation of benzylic C–H bonds under iron catalysis DOI

Rui Qi,

Tianwen Bai,

Shuwang Tang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(26), С. 5382 - 5386

Опубликована: Янв. 1, 2023

This paper describes the iron-catalyzed photochemical carbonylation of benzylic C-H bonds resulting in synthesis various aryl ketones. Using 5 W blue LED irradiation, reactions proceed smoothly presence 2 mol% FeBr3 MeOH at 35 °C. The catalytic system could be extended for oxidation silane, thioether, and phosphine into silenol, sulphoxide, phosphoxide, respectively. A mechanistic study suggests that a hydrogen bond-stabilized iron-hydroperoxo species is reactive intermediate. It shown reaction proceeds via four-electron-transfer pathway, cation seems to crucial species. method applied pomalyst, haloperidol, melperone, lenperone.

Язык: Английский

Процитировано

8

β-Scission of Secondary Alcohols via Photosensitization: Synthetic Utilization and Mechanistic Insights DOI Creative Commons
Yeersen Patehebieke,

Rima Charaf,

Hogan P. Bryce-Rogers

и другие.

ACS Catalysis, Год журнала: 2023, Номер 14(1), С. 585 - 593

Опубликована: Дек. 26, 2023

An efficient metal-free photocatalytic method for the alkylation of alkenes using accessible aliphatic alcohols as redox auxiliaries is presented. C-centered radicals can be generated under mild conditions and subsequently employed in a C(sp3)–C(sp3) bond-forming process, which overall provides C1 tethering strategy nucleophiles electrophiles. The optimized accommodate various electron-deficient secondary/tertiary alcohols, with applications late-stage functionalization natural products pharmaceutically relevant compounds. Mechanistic investigations revealed complex mechanistic manifold, including non-PCET fragmentation concerted/stepwise PCET. Even though previously thought PCET type mechanism compatible our observations, most probably constitutes main pathway.

Язык: Английский

Процитировано

8

Direct Alkene Functionalization via Photocatalytic Hydrogen Atom Transfer from C(sp3)–H Compounds: A Route to Pharmaceutically Important Molecules DOI

Hangqian Fan,

Yuxin Fang, Jingbo Yu

и другие.

Chemical Communications, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Direct functionalization of alkenes with C(sp

Язык: Английский

Процитировано

3