Cobalt-Catalyzed Three-Component Alkyl Arylation of Acrylates with Alkyl Iodides and Aryl Grignard Reagents DOI

Lei Xu,

Fan Zhang, Yan‐En Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9288 - 9293

Published: Oct. 21, 2024

A highly regioselective cobalt-catalyzed three-component alkyl arylation of acrylates with iodides and aryl Grignard reagents has been established. The reaction efficiently provides an alternative strategy for the construction α-aryl esters a broad substrate scope good yields under mild conditions. practical applicability this protocol is shown by scaled-up further transformations products. In addition, preliminary mechanistic explorations demonstrated that radicals generated efficient cobalt catalysis are instantaneously added to finally afford desired

Language: Английский

Merging Photoinduced Electron Transfer with Hydrogen Atom Transfer: Formal β-C(sp3)–H Pyridination of Carbonyls DOI
Jian Li, Jun Xu, Binbin Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

In this study, a novel approach that combines photoinduced electron transfer (ET) with hydrogen atom (HAT) has been introduced for the selective β-C(sp3)–H pyridination of carbonyl compounds. This method is notable its absence transition metals and ability to function under benign reaction conditions, resulting in range pyridinated derivatives consistently moderate good yields. The significance technique further underscored by potential late-stage functionalization pharmaceutically significant molecules. Mechanistic investigations confirmed proceeds via radical-mediated pathway.

Language: Английский

Citations

4
Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1H)-ones with Aldehydes under Mild Conditions DOI
Hong Yu, Jun Xu, Chen An

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(10), P. 2526 - 2531

Published: March 5, 2025

Herein, we introduce an efficient and straightforward strategy for the selective C-H esterification alkylation of quinoxalin-2(1H)-ones with aldehydes. A key feature our study is ability to perform both using different types The reaction system highly compatible a range aldehydes, yielding C3-esterified C3-alkylated products in moderate-to-good yields. applicability this approach further enhanced by its scalability through continuous-flow synthesis, late-stage modification significant molecules, product derivatization. Our mechanistic investigations reveal radical relay mechanism, triggered hydrogen atom transfer process.

Language: Английский

Citations

4
N-Phenylphenothiazine-based Hyper-cross-linked Polymers for Recyclable, Heterogeneous Photocatalysis of Organic Transformations: A Strategy to Access 6-Difluoromethyl-phenanthridines DOI

Shengjie Song,

Wenjian Wang,

Yali He

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 23, 2025

Herein, a N-phenylphenothiazine-based hyper-cross-linked polymer (PTH-HCP) was finely designed and constructed, which serves as metal-free heterogeneous photocatalyst for organic transformations. Characterization experiments have shown that this demonstrates outstanding stability, extensive surface area, exceptional photoelectric response properties. Moreover, PTH-HCP showed good catalytic efficiency recyclability in the photochemically driven difluoromethylation/cyclization reactions. This work provides strategy design construction of photocatalysts offers support their broad prospects synthetic applications.

Language: Английский

Citations

1
Organic Photoredox Catalytic Difluoroalkylation of Unactivated Olefins to Access Difluoro-Containing Tetrahydropyridazines DOI

Jun Sun,

Yu Wei,

Ting Lv

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9973 - 9977

Published: Nov. 14, 2024

Herein, we disclose a readily available phenothiazine derivative as an organocatalyst, which upon excitation with 371 nm light acquires strongly reducing power and serves to induce the radical cascade difluoromethylation/cyclization reaction of

Language: Английский

Citations

3
Biomimetic Dehydrogenative Intermolecular Formal Allylic Amidation of Branched α‐Olefins DOI Creative Commons
Xiaoyang Fu,

Jiarui Tian,

Mingjun Zhang

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 12(2)

Published: Nov. 18, 2024

Abstract Allylic amide moieties are commonly encountered in natural products and privileged structures pharmaceuticals agrochemicals. Moreover, because allylic can be to converted into an array of high‐value motifs, they have been widely employed organic synthesis. However, the development catalytic systems for intermolecular amidation olefins, particularly branched α ‐olefins, has proven challenging. Here, a biomimetic, synergistic method is reported that combines photoredox, cobalt, Brønsted base catalysis synthesis substituted amides from ‐olefins simple imides without using oxidants. This low‐cost, operationally features broad substrate scope excellent functional group compatibility. it successfully used functionalization several structurally complex molecules demonstrating method's potential utility medicinal chemistry applications. Mechanistic studies revealed C( sp 3 )─N bond formation mediated by nitrogen‐centered radical intermediate, which generated via sequence involving deprotonation single‐electron oxidation.

Language: Английский

Citations

3
Photocatalytic Decarboxylative Cross-Coupling of α,β-Unsaturated Acids with Amines for α-Ketoamides via C–N Bond Formation DOI

Soumya Mondal,

Suman Das,

Subal Mondal

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16750 - 16758

Published: Nov. 5, 2024

An unprecedented oxidative decarboxylative chemical domain of α,β-unsaturated acids and amines for C-N cross-coupled α-ketoamidation is disclosed. Molecular oxygen as a source in amide water the ketone segment furnished green sustainable synthesis α-ketoamide from feedstock amines. Mechanistically, photocatalyst travels with reductive quenching cycle, whereas pallado-cycle proceeded through bond formation. Broad substrate scope, functional group tolerance, CO

Language: Английский

Citations

2
Electrochemical 1,2-hydrogen atom transfer functionalizations of N-(benzyloxy)phthalimides DOI

Xin Fu,

Tingting Ran,

Jie Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6760 - 6767

Published: Jan. 1, 2024

We describe a straightforward and efficient electrochemical approach for the cathodic benzylic C–H hydroxyalkylation arylation of N -(alkyloxy)phthalimides mediated by 1,2-HAT alkoxy radicals.

Language: Английский

Citations

0
Cobalt-Catalyzed Three-Component Alkyl Arylation of Acrylates with Alkyl Iodides and Aryl Grignard Reagents DOI

Lei Xu,

Fan Zhang, Yan‐En Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9288 - 9293

Published: Oct. 21, 2024

A highly regioselective cobalt-catalyzed three-component alkyl arylation of acrylates with iodides and aryl Grignard reagents has been established. The reaction efficiently provides an alternative strategy for the construction α-aryl esters a broad substrate scope good yields under mild conditions. practical applicability this protocol is shown by scaled-up further transformations products. In addition, preliminary mechanistic explorations demonstrated that radicals generated efficient cobalt catalysis are instantaneously added to finally afford desired

Language: Английский

Citations

0