Photoinduced Radical Relay Reaction of 2-Methylthiolated Phenylacetylenes/Alkynones Initiated by Electron Donor–Acceptor Complexes DOI
Jie Sun, Lijun Zheng, Heng Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 19, 2024

A method was found to construct sulfur-containing five- and six-membered heterocyclic alkyl sulfonyl compounds by using visible light free radicals activated and/or generated EDA complexes/homolytic cleavage as initiators stimulate the relay reaction of alkynes/alkynones. This puts forward a new strategy initiate sulfonation alkynes/alkynones with only catalytic amount initiator. generating initiator complex activation/homolytic provides idea for following substances that must be excited.

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

Multicomponent Synthesis of Alkyl BCP-Heteroaryls via Electron Donor–Acceptor Complex Photoactivation under Mild Conditions DOI
Yanhe Li, Jun Xu, Yuxin Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1683 - 1696

Published: Jan. 17, 2025

In the vanguard of sustainable chemistry, pursuit efficient pathways for synthesis alkyl bicyclo[1.1.1]pentane-heteroaryls has captured attention scientific vanguard. We herein report a groundbreaking and eco-conscious multicomponent coupling reaction that paves way alkylation heteroarylation [1.1.1]propellane, process uniquely enabled by photochemical prowess an electron donor–acceptor (EDA) complex. This method is distinguished its minimalist yet powerful approach: devoid transition metals, additives, photosensitizers. Its universality further exemplified seamless compatibility broad spectrum halides heteroarenes under standardized conditions, heralding new era synthetic versatility. The method's practicality underscored capacity late-stage modification pharmaceuticals, offering transformative tool enhancement existing drug molecules. Moreover, facile derivatization synthesized products underscores adaptability potential diverse applications. Our mechanistic studies have elucidated underlying radical-relay pathway, pinpointing pivotal role EDA complex in initiating transformation. discovery not only enriches our fundamental understanding but also opens avenues strategic optimization.

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

3

A General Approach for the Synthesis of Cyanoisopropyl Bicyclo[1.1.1]pentane (BCP) Motifs by Energy Transfer Process DOI
Lin Li, Qing Pang, Binbin Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(33), P. 7060 - 7065

Published: Aug. 13, 2024

Bicyclo[1.1.1]pentane (BCP) heteroaryls make up an important class of BCP derivatives in drug discovery. Herein, we report the visible-light-mediated synthesis cyanoisopropyl BCP-heteroaryls motifs from

Language: Английский

Citations

16

Transition-metal-, oxidant- and additive-free multi-component synthesis of alkyl heteroaryl BCPs enabled by visible-light-induced phosphine-catalyzed halogen-atom transfer DOI
Jun Xu,

Yu Hong,

Ruiyuan Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This study describes a pioneering visible-light-induced phosphine-catalyzed halogen-atom transfer (XAT) strategy that heralds new era in the difunctionalization of [1.1.1]propellane.

Language: Английский

Citations

12

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

Synthesis of Nafimidone Derivatives by Visible-Light-Induced α-C—H Functionalization of Carbonyl DOI
Jiabin Shen, Chao Shen, Pengfei Zhang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 677 - 677

Published: Jan. 1, 2025

Language: Английский

Citations

1

A Mechanistic Perspective on Photocatalytic EnT-Enabled C3-N-Heteroarylation of Aryl Quinoxaline via C(sp2)–C(sp2) Coupling DOI
Raju Mandal, Subhendu Ghosh,

Sayan Laha

et al.

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

Published: April 11, 2025

An EnT-mediated C3-N-heteroarylation of 2-aryl quinoxalines via decarboxylative radical-radical cross-coupling (C(sp2)-C(sp2)) with oxime esters is presented. Upon photoactivation, the triplet energy photocatalyst transferred to both reacting partners (oxime ester and 2-phenylquinoxaline). The excited undergoes fragmentation a C-centered N-heteroaryl radical an N-centered imine radical. former attacks C3 site quinoxaline diradical, while latter acts as hydrogen atom abstractor (HAA). Computational studies revealed that C-C bond formation heteroaryl energetically more favorable than C-N formation.

Language: Английский

Citations

0

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

Self-Catalyzed Sono-Photoinduced Arylation of Quinoxalin-2(1H)-ones with Arylhydrazines DOI

Yao-Dan Xu,

Yang Xing,

Hong‐Tao Ji

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

Herein, the first example of self-catalyzed sono-photoinduced carbon-carbon bond formation was described. Combining advantages phototriggered self-catalysis and ultrasonic catalysis, a wide range 3-arylquinoxalin-2(1

Language: Английский

Citations

3