Visible-Light-Promoted Radical Cascade Sulfone Alkylation/Cyclization of 2-Isocyanoaryl Thioethers Enabled by Electron Donor–Acceptor Complex Formation DOI

Jiamei Shen,

Hui Li, Li Yuan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10223 - 10233

Published: June 28, 2024

A photo-induced cascade sulfone alkylation/cyclization of 2-isocyanoaryl thioethers is explored. This visible-light-triggered reaction not only occurs under extremely mild conditions but also does require the presence a photosensitizer. The photocatalytic process triggered by photochemical activity in situ-generated electron donor–acceptor complexes, arising from association and α-iodosulfones. radical pathway was confirmed UV–vis spectroscopy, trapping, Job's plot, on/off irradiation experiments.

Language: Английский

Photocatalytic cyclization of 3-(2-isocyanophenyl)quinazolin-4(3H)-ones for the construction of quinoxalino[2,1-b]quinazolinones DOI

Xian Wu,

Ling-Li Liu,

Chengli Xiang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(18), P. 2556 - 2559

Published: Jan. 1, 2024

3-(2-Isocyanophenyl)quinazolin-4(3 H )-ones were designed and synthesized as new building units for the construction of novel quinoxalino[2,1- b ]quinazolinones under mild, photocatalytic metal-free conditions.

Language: Английский

Citations

5

Photo-induced phosphorylation/cyclization of N-homoallyl and N-allyl aldehyde hydrazones to access phosphorylated tetrahydropyridazines and dihydropyrazoles DOI
Ling-Li Liu,

Yechun Wu,

Chengli Xiang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(35), P. 4687 - 4690

Published: Jan. 1, 2024

A visible-light-induced carbophosphorylation/cyclization of N -homoallyl and -allyl aldehyde hydrazones with phosphine oxides was developed to obtain phosphorylated tetrahydropyridazines dihydropyrazoles.

Language: Английский

Citations

5

1,3-Difunctionalization of Alkenes by Cobaloxime Photocatalysis DOI

Jixin Yu,

Yuanyuan Cheng,

Xin-Yi Zeng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6809 - 6813

Published: Aug. 5, 2024

Represented herein is the first 1,3-difunctionalization of alkenes via photocatalysis. A single cobaloxime used to carry out two catalytic cycles in which not only as a photocatalyst initiate reaction but also metal catalyst for β-H elimination process. Electron-deficient alkenes, electron-rich and unactivated could be directly converted 1,3-bisphosphorylated products, even unsymmetric with H

Language: Английский

Citations

4

Direct Excitation of Aldehyde to Activate the C(sp2)−H Bond by Cobaloxime Catalysis toward Fluorenones Synthesis with Hydrogen Evolution DOI
Jia‐Dong Guo,

Ya‐Jing Chen,

Chenhong Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(7)

Published: Dec. 13, 2022

A new way to form fluorenones via the direct excitation of substrates instead photocatalyst activate C(sp2 )-H bond under redox-neutral condition is reported. Our design relies on photoexcited aromatic aldehyde intermediates that can be intercepted by cobaloxime catalyst through single electron transfer for following β-H elimination. The generation acyl radical and successful interception a metal avoid use stoichiometric external oxidants, affording series highly substituted fluorenones, including six-membered ketones, such as xanthone thioxanthone derivatives in good excellent yields, with hydrogen only byproduct. This catalytic system features readily available catalyst, mild reaction conditions broad substrate scope, which sunlight scale-up experiments continuous-flow approach make methodology sustainable amenable potentially operational procedures.

Language: Английский

Citations

18

Photoinduced Co-catalyzed dehydrogenative cyclization of 2-alkenylphenyl carbonyl compounds and mechanistic insights DOI
Haoyuan Li, Xiu‐Long Yang, Feng Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We present two protocols for the efficient synthesis of substituted 1-naphthols. DFT calculations and verification experiments elucidate mechanism. Scale-up product conversion confirm reaction's practical potential.

Language: Английский

Citations

0

Photoinduced Cobaloxime-Catalyzed Regio- and Diastereoselective Hydrogen-Evolution C(sp3)–H Phosphorylation of Bicyclo[1.1.0]butanes DOI
Pengfei Chen,

Meng-Yuan Dong,

Chun-Yu Han

et al.

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

Published: Jan. 15, 2025

Radical-initiated functionalization of bicyclo[1.1.0]butanes (BCBs) is a straightforward approach to accessing diverse cyclobutane derivatives. However, selective C(sp3)–H at the C2 position BCBs remains scarce. Herein, mild protocol for hydrogen-evolution phosphorylation with enabled by photoinduced cobaloxime catalysis was realized in regio- and diastereoselective manner. This oxidant- additional photocatalyst-free method wide range diarylphosphine oxides. The mechanism studied via control experiments DFT calculation. Moreover, efficiency this highlighted synthesis high-value, structurally complex molecules.

Language: Английский

Citations

0

Unlocking Isonitrile Insertion with N-Centered Radicals: A General Synthetic Strategy toward Quinazolinone Alkaloids by Synergistic Photo/Copper Catalysis DOI
Xiao-Yu Guo, Hui Wang,

Zhongyan Hu

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 5307 - 5317

Published: March 16, 2025

Language: Английский

Citations

0

Visible Light‐Induced Arylation/Alkylation/Phosphorylation of Isocyanides viaEDA Complex Activation DOI Open Access

Shichao Yang,

Xiangwen Tan,

Dan Liu

et al.

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

Published: March 20, 2025

Comprehensive Summary Herein, it is reported that the aryl radicals derived from thianthrenium salts are used as coupling partner in arylation reactions of isocyanides, simultaneously initiators for formation alkyl and phosphoryl ethers diarylphosphine oxides. This cascade cyclization reaction leads to diverse arylated, alkylated phosphorylated heteroaromatic compounds. Notably, this transformation can be achieved without aid metals or photocatalysts, exhibiting a wide substrate applicability operational simplicity. Mechanistic studies suggest involvement radical processes electron donor‐acceptor (EDA) complexes transformation.

Language: Английский

Citations

0

Visible-light-induced radical cascade cyclization of 2-isocyanobiaryls via 1,5-hydrogen atom transfer (1,5-HAT) DOI

Yafei Zhu,

Penghua Zhang,

Xingqin Tian

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We reported the first example of visible-light-induced radical cascade cyclization 2-isocyanobiaryls via 1,5-HAT, which is characterized by broad substrate scope, excellent functional group compatibility and no requirement any metals base.

Language: Английский

Citations

0

Visible light-mediated synthesis of 1,3-benzothiazoles: A comprehensive review DOI
Vitalii A. Palchykov

Coordination Chemistry Reviews, Journal Year: 2025, Volume and Issue: 537, P. 216677 - 216677

Published: April 14, 2025

Language: Английский

Citations

0