Photo‐catalyzed Stereospecific Synthesis of Trisubstituted Alkenes Incorporating 3,3‐Difluoro‐γ‐Lactams from Morita‐Baylis‐Hillman Acetates and N‐Allylbromodifluoroacetamides DOI Open Access
Xi Chen,

Chi Ai,

Yuting Wang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Abstract A photocatalytic methodology has been devised for the stereoselective construction of trisubstituted alkenes incorporating 3,3‐difluoro‐γ‐lactams in 17–93% yields via a radical cascade process utilizing MBH acetates and N ‐allylbromodifluoroacetamides as starting materials. The reaction mechanism involves single‐electron transfer, 5 ‐ exo trig cyclization, addition, elimination fashion.

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

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

Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides DOI
Zhixian Yang,

Lu-Cai Ding,

Gui-Hong Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10660 - 10677

Published: July 18, 2024

Two general protocols for the regioselective electrochemically enabled sulfonylation cyclization of

Language: Английский

Citations

8

Photo-promoted radical cascade cyclization of 4-(allylamino)-3-cyanocoumarins: access to sulfonylated pyrido[3,2-c]coumarin derivatives DOI
Luyao Yang, Jun Ying, Hao Zheng

et al.

Green Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The first method for constructing pyrido[3,2- c ]coumarin derivatives via a radical cascade cyclization process was proposed, which can introduce active fragments.

Language: Английский

Citations

0

Metal-free three-component reactions of alkynes for the construction of 3,4-difunctionalized benzo[h]coumarins DOI

Shendan Xia,

Chaojie Wang,

Yuyan Xu

et al.

New Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel approach for constructing 3,4-difunctionalized benzo[ h ]coumarins through a metal-free multicomponent reactions with mild reaction conditions.

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

DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes DOI

Lu-Cai Ding,

Gui-Hong Yang,

Li Luo

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

Comprehensive Summary Herein, we report a rare example of three‐component net‐oxidative sulfonylation SO 2 surrogate with an oxidatively activated radical precursor under mild and metal‐ external‐oxidant‐free conditions. The mildness sustainability the reaction are enabled by photoelectrocatalysis, 3‐aza‐1,5‐dienes, organotrifluoroborates 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in atom‐economical manner broad substrate scope good functional‐group tolerance. protocol is amenable late‐stage diversification complex molecular architectures as well gram‐scale synthesis. Sunlight could be used light source, conducted all‐solar mode using commercially available photovoltaic panel generate electricity situ . Mechanistic studies reveal that generated (DABCO), which was generally innocent previous reactions, functions electron shuttle between photocatalytic cycle reactants.

Language: Английский

Citations

2

Photo-Induced Difluoroalkylation/Cyclization of Alkyne Ketones: A Novel Strategy to Access Difluoroalkyl Thiofavones DOI

Shengjie Song,

Can Luo,

Guan Wang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A photo-induced electron donor-acceptor (EDA) complex enabled tandem reaction of alkyne ketones

Language: Английский

Citations

1

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

Citations

0