Catalyst-Free, Multicomponent Reaction of Iodonium Ylides, Nitrosoarenes, and Olefins for the Synthesis of Isoxazolidine Derivatives DOI
Lei Li, Jun Xuan,

Yan‐Rui Zhao

et al.

Synlett, Journal Year: 2023, Volume and Issue: 34(17), P. 2022 - 2028

Published: June 7, 2023

Abstract A general and efficient three-component protocol for the synthesis of isoxazolidines has been developed. range nitrosoarenes, olefins, as well iodonium ylides can be subjected to this reaction generate N-aryl derivatives with moderate excellent yields. In addition, we demonstrate that approach employs 1,3-dipolar cycloaddition nitrones generated in situ from nitroso compounds, olefins absence any catalysts additives.

Language: Английский

Advances in heterocycle synthesis through photochemical carbene transfer reactions DOI
Ziyi Xie, Jun Xuan

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(16), P. 2125 - 2136

Published: Jan. 1, 2024

In this feature article, we focus on the photochemical strategy for construction of heterocyclic skeletons, specifically highlighting methods that employ visible light-promoted carbene transfer reactions.

Language: Английский

Citations

22

Photodriven Radical-Polar Crossover Cyclization Strategy: Synthesis of Pyrazolo[1,5-a]pyridines from Diazo Compounds DOI
Peng Zhao, Yanbo Liu, Yuting Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2511 - 2516

Published: March 20, 2024

This work demonstrates the synthesis of a variety perfluoroalkyl heterocycles via visible-light-driven radical-polar crossover cyclization strategy. In this process, single-electron reduction/SNV-type/cyclization sequences follow radical addition reaction diazoester, which differs from current role diazoesters as precursors/acceptors. transformation excellent functional group compatibility and allows for modification many bioactive molecules with diazoesters. Such could represent novel approach to photochemical diazo compounds.

Language: Английский

Citations

18

Photocatalytic Synthesis of Indanone, Pyrone, and Pyridinone Derivatives with Diazo Compounds as Radical Precursors DOI
Yang Xie,

Ye‐Peng Bao,

Xiao-Yan Zhuo

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1393 - 1398

Published: Feb. 12, 2024

We disclose herein a photocatalytic radical cascade cyclization of diazoalkanes for the divergent synthesis important carbocycles and heterocycles. Under optimal reaction conditions, various indanone, pyrone, pyridinone derivatives can be obtained in moderate to good yields. Mechanistic experiments support formation carbon-centered radicals from through proton-coupled electron transfer process. Scale-up using continuous flow technology useful downstream application formed heterocycles further render strategy attractive valuable.

Language: Английский

Citations

10

Carbene-induced ring-opening reactions of five-/six-membered cyclic ethers: expanding the frontiers of functional group introduction and molecular architecture construction DOI
Jun Xiao,

Dandan Jiang,

Xiujuan Wu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The multi-component ring-opening reactions of cyclic ethers offer an efficient strategy for the rapid introduction multiple functional groups and construction complex molecular architectures.

Language: Английский

Citations

0

Photoinduced Formal Cross-[3+3] Cycloaddition of Vinyldiazo Reagents with Acceptor-Only Diazoalkanes DOI
Yang Xie, Lihua Zhang, Jun Xuan

et al.

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

Published: March 22, 2025

In this study, we devised an innovative approach for the synthesis of pyrazine derivatives through a photoinduced formal cross-[3+3] cycloaddition between vinyldiazo reagents and acceptor-only diazoalkanes. This method leverages differential reactivity two distinct diazo compounds: reagents, which upon visible light irradiation form key cyclopropane intermediates, diazoalkanes, function as 1,3-dipoles to capture photogenerated reactive species. The reactions proceed exclusively under light, yielding 1,4-dihydropyridazines with broad substrate scope compatibility various functional groups. Importantly, synthesized can be readily converted other valuable products. mechanism, elucidated UV–vis absorption studies, deuterium labeling experiments, control in situ NMR spectroscopy, provides clear understanding observed reactivity.

Language: Английский

Citations

0

Photoinduced [3+2] Cycloaddition of Alkyl–Acceptor Diazoalkanes: Diversity-Oriented Synthesis of Pyrazolines Containing a Quaternary Center DOI

Fengya He,

Ziyi Sun,

Yiwei Xu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(19), P. 4031 - 4036

Published: Jan. 26, 2024

We present a new [3+2] cycloaddition reaction between alkyl-acceptor diazoalkanes under visible light irradiation. By employing easily accessible alkyl-acceptor-type or their precursor hydrazones as both 1,3-dipoles and dipolarophiles, diverse range of pyrazoline derivatives featuring quaternary center have been efficiently synthesized in predictable manner, with excellent functional group tolerance good yields. Furthermore, scale-up experiments downstream transformations the product were also detailed.

Language: Английский

Citations

2

Photochemical Synthesis of 1,4‐Dicarbonyl Containing Quinoxalin‐2(1H)‐Ones through Consecutive Photoredox Catalysis DOI

Cong‐Lun Xu,

Ye‐Peng Bao,

Yang Xie

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1833 - 1839

Published: Feb. 8, 2024

Abstract Herein, we report a photochemical synthesis of 1,4‐dicarbonyl containing quinoxalin‐2(1 H )‐ones through consecutive photoredox catalysed reactions. A wide range C3‐modified were obtained in 53–91% yields by this approach. Mechanistic studies including radical trapping, EPR studies, D‐labelling investigations, and many other control experiments well explained the proposed mechanism.

Language: Английский

Citations

2

Photoinduced Asymmetric Formal Siloxycarbene Insertion into sp3 C–H Bonds Enabled by Chiral Phosphoric Acid DOI
Ziyi Xie, Qiang‐Qiang Li, Yang Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5827 - 5832

Published: July 2, 2024

We disclosed herein an enantioselective formal siloxycarbene insertion reaction enabled by chiral phosphoric acid and blue LED irradiation. This is the first time asymmetric into sp

Language: Английский

Citations

2

Photoredox-enabled remote radical group migration: Pathway to 1,7-dicarbonyl compounds from diazoalkanes DOI Creative Commons

Hai‐Bing Ye,

Ye‐Peng Bao,

Tianyang Liu

et al.

Tetrahedron Chem, Journal Year: 2023, Volume and Issue: 7, P. 100040 - 100040

Published: June 16, 2023

Herein, we developed a mild and efficient photoredox-enabled remote radical group migration with the utilization of diazoalkanes as precursors, giving access to various valuable 1,7-dicarbonlys in moderate good yields. A diverse set migrating groups, including benzothiazole, benzothiophene, pyrazine, pyridine, thiazole, thiophene nitrile were well tolerated. Furthermore, facile synthesis 1,8-dicarbonyl compound, scale-up reaction useful synthetic transformation further proved method attractive valuable.

Language: Английский

Citations

2

Catalyst-free synthesis of hydrazino-containing glycine derivatives via a diaziridine in-situ formation/ring-opening cascade DOI

Chang-Long Rong,

Qiang‐Qiang Li, Jun Xuan

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(16), P. 9104 - 9109

Published: Jan. 1, 2024

A green and efficient method for the synthesis of glycine derivatives from amines, azodicarboxylates, diazoalkanes has been developed. This multicomponent reaction occurred under mild conditions in absence any catalysts or additives.

Language: Английский

Citations

0