Magnesium-Mediated Umpolung Carboxylation of p-Quinone Methides with CO2 DOI

Yunying Yan,

Jianjun Hao,

Fenfen Xie

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(20), P. 14640 - 14648

Published: Sept. 29, 2023

Magnesium-mediated reductive carboxylation of p-QMs with CO2 via an Umpolung strategy has been developed, which can be used for the preparation various aryl acetic acids. This protocol featured high atom economy, mild conditions, and operational simplicity. The creation this will unprecedentedly extend application to nucleophilic reagents.

Language: Английский

Recent advances in photo- and electro-enabled radical silylation DOI
Liqing Ren, Na Li, Jie Ke

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(22), P. 6400 - 6415

Published: Jan. 1, 2022

This review aims to highlight the recent advances in area of radical type silylation reactions mediated by photo- and electrocatalysis.

Language: Английский

Citations

62
Photoredox Metal-Free Allylic Defluorinative Silylation of α-Trifluoromethylstyrenes with Hydrosilanes DOI
Cong Luo, Yang Zhou, Hang Chen

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(23), P. 4286 - 4291

Published: June 8, 2022

We report an efficient strategy that combines organic photoredox and hydrogen atom transfer to deliver gem-difluoroallylsilanes via defluorinative silylation of α-trifluoromethylstyrenes using hydrosilanes as silicon sources. This protocol provides environmentally friendly approach for the preparation structurally diverse with excellent functional group compatibility renders it suitable late-stage modification bioactive complex molecules.

Language: Английский

Citations

45
Recent Advances on C—H Functionalization via Oxidative Electrophotocatalysis DOI

Aman Hasil,

Rui Chang,

Juntao Ye

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 728 - 728

Published: Jan. 1, 2024

Language: Английский

Citations

8
Multicomponent Synthesis of S-Benzyl Dithiocarbamates from para-Quinone Methides and Their Biological Evaluation for the Treatment of Alzheimer’s Disease DOI
Rapelly Venkatesh, Gauri Shankar,

Aswathi C. Narayanan

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(10), P. 6730 - 6741

Published: May 12, 2022

Multicomponent synthesis of biologically relevant S-benzyl dithiocarbamates from para-quinone methides, amines, and carbon disulfide are described under catalyst additive-free conditions. The reactions proceeded at room temperature in a short span time with excellent yields. One the synthesized compounds, 3e showed considerable acetylcholinesterase (AChE) inhibitory (51.70 + 5.63% 20 μm) antioxidant (63.52 ± 1.15 activities.

Language: Английский

Citations

28
Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with p-quinone methides under metal- and additive-free conditions DOI

Tongyao Zhou,

Jie Zeng, Yang Liu

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(3), P. 1375 - 1380

Published: Jan. 1, 2024

A visible-light-mediated tandem ring opening/1,6-conjugate addition of cyclobutanols with p -quinone methides was developed. This protocol allowed the formation δ,δ-diaryl ketones in presence a readily available organic photocatalyst.

Language: Английский

Citations

5
Visible Light-Induced Diastereoselective Construction of Trifluoromethylated Cyclobutane Scaffolds through [2+2]-Photocycloaddition and Water-Assisted Hydrodebromination DOI
Xiao Hu,

Weibo Xu,

Yin Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(4), P. 2521 - 2534

Published: Jan. 26, 2023

A visible light-induced diastereoselective synthesis of trifluoromethylated cyclobutane derivatives is described, consisting [2+2]-photocycloaddition and water-assisted hydrodebromination by one pot. Quinolinones, isoquinolinones, coumarins are able to participate in this one-pot process with 1-bromo-1-trifluoromethylethene. In addition, stereodefined trisubstituted alcohols, carboxylic acids, amines can be obtained a straightforward manner through the ring opening lactone or lactam without loss original high diastereoselectivity given water-tristrimethylsilylsilane coordination. The antineoplastic bioactivities those compounds also well studied, which exhibit great potential comparable cisplatin. proposed mechanism, thioxanthone (TX) serves as dual catalyst radical chain pathway may involved process.

Language: Английский

Citations

12
Theoretical study of an N-heterocyclic carbene-catalyzed annulation reaction between an enal and a β-silyl enone: Mechanism and origin of stereoselectivity DOI
Yang Wang,

Yilu Luo,

M. Zhao

et al.

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 551, P. 113621 - 113621

Published: Oct. 27, 2023

Language: Английский

Citations

11
Photocatalytic synthesis of alkyl–alkyl sulfonesviadirect C(sp3)–H bond functionalization DOI

Wenhua Lu,

Dan Yang, Guoqin Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(13), P. 2822 - 2827

Published: Jan. 1, 2023

We report a highly efficient one-pot, three-component strategy for the construction of alkyl-alkyl sulfones through photoinduced TBADT-catalyzed C(sp3)-H sulfonylation unactivated hydrocarbon compounds. A wide range commercially available compounds and bioactive molecules can be successfully applied to catalytic system, affording corresponding in good excellent yields (>50 examples, up 87% yield).

Language: Английский

Citations

10
Photoredox Synthesis of Silicon-Containing Isoindolin-1-ones and Deuterated Analogues Through Hydrosilylation and Deuterium-silylation DOI
Guoqin Wang, Yue Zhang,

Yuan‐Xia Zhou

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7899 - 7912

Published: May 10, 2024

An efficient, practical, and metal-free protocol for the synthesis of silicon-containing isoindolin-1-ones deuterated analogues via synergistic combination an organic photoredox hydrogen atom transfer process is described. This strategy features mild reaction conditions, high economy, excellent functional group compatibility, delivering a myriad structurally diverse valuable products with good to yields.

Language: Английский

Citations

3
Directed Palladium‐Catalyzed pseudo‐Anomeric C−H Functionalization of Glycal‐Type Substrates: Access to Unsymmetrical gem‐Diarylmethyl C‐Glycosides DOI
Atul Dubey,

Neha Singh Chauhan,

Zanjila Azeem

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(6), P. 820 - 825

Published: Feb. 22, 2023

Pd(II)-Catalyzed, bidentate directing group (BDG)-assisted C(sp2)−H functionalization of C2-amido glycals onto the anomeric position is described as a contemporary method for construction various unsymmetrical gem-diarylmethyl C-glycosides. Thanks to amidoquinoline-type group, insertion diverse para-quinone methides (p-QMs) pseudo-anomeric glycal substrates were executed in moderate good yields. Further final product can be successfully demonstrated by known palladium-catalyzed cross-coupling reactions. As service our authors and readers, this journal provides supporting information supplied authors. Such materials are peer reviewed may re-organized online delivery, but not copy-edited or typeset. Technical support issues arising from (other than missing files) should addressed Please note: The publisher responsible content functionality any Any queries content) directed corresponding author article.

Language: Английский

Citations

7