Palladium-Catalyzed Synthesis of α-Fluoro Olefins via C–H/C–F Coupling DOI
Mark Lautens, Colton E. Johnson

Synfacts, Journal Year: 2023, Volume and Issue: 20(01), P. 0047 - 0047

Published: Dec. 8, 2023

Key words palladium catalysis - defluorination C–H activation DFT calculations

Language: Английский

Extended π-conjugated systems by external ligand-assisted C−H olefination of heterocycles: Facile access to single-molecular white-light-emitting and NIR fluorescence materials DOI

Ruike Hu,

Kangmin Wang,

Junxiang Liu

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110113 - 110113

Published: June 1, 2024

Language: Английский

Citations

5
N‐Heterocyclic Carbene Organocatalysis Enabled Modular Synthesis of Fluorinated Isoflavonoids to Suppress Proliferation and Migration in Breast Cancer Cells DOI Creative Commons
Yanqing Liu, Leilei Fu,

Liwu Hong

et al.

Advanced Science, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 13, 2025

Abstract Isoflavonoids represent a privileged scaffold among various bioactive natural products, rendering their structural diversification through green synthesis and subsequent biological evaluations compelling research area. In this study, an NHC organocatalytic radical acylalkylation of 1,3‐enynes using salicylaldehydes is presented, followed by cascade intramolecular annulation, yielding series fluorinated isoflavone derivatives with substantial yields under environmental‐friendly conditions. This approach, distinguished its excellent modularity high functional group tolerance, represents unprecedented 1,3,4‐trifunctionalization designed for the isoflavones in single step. Furthermore, it demonstrated that these synthesized isoflavonoids effectively suppress proliferation breast cancer cells, most potent compound 8 also inhibiting migration MDA‐MB‐231 cells.

Language: Английский

Citations

0
A highly efficient approach to Z-monofluoroolefin-dehydroamino acid derivatives from gem-difluoroalkenes DOI

Chuangchuang Liu,

Yilian Song,

Wenjie Ju

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111167 - 111167

Published: April 1, 2025

Language: Английский

Citations

0
Remote meta-C–H α-Fluoro-alkenylation of Arenes Using gem-Difluoroalkenes DOI
Yogesh Bairagi,

Sandip Porey,

Iti Mahato

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7536 - 7542

Published: April 22, 2025

Citations

0
Synthesis of gem-difluorinated pentacyclic indenopyrazolopyrazolones via Rh(iii)-catalyzed cascade C–H functionalization/[3 + 2] dipolar cycloaddition DOI

Fu‐Xiaomin Liu,

Weijie Chen, Ying Cai

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2512 - 2517

Published: Jan. 1, 2024

A Rh( iii )-catalysed cascade C–H functionalization/[3 + 2] dipolar cycloaddition was realized to deliver gem -difluorinated pentacyclic indenopyrazolopyrazolones with four continuous chiral carbon centres in a one-pot fashion.

Language: Английский

Citations

3
Palladium and Copper Co-Catalyzed Chloro-Arylation of gem-Difluorostyrenes – Use of a Nitrite Additive to Suppress β-F Elimination DOI Creative Commons
Andrew J. Intelli,

Coriantumr Z. Wayment,

R. T. LEE

et al.

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

Published: Jan. 1, 2024

The installation of fluorine and fluorinated functional groups in organic molecules perturbs the physicochemical properties those enables development new therapeutics, agrichemicals, biological probes materials. However, current synthetic methodologies cannot access some scaffolds. One such group,

Language: Английский

Citations

2
Synthesis of β-(Hetero)aryl Ketones via Ligand-Enabled Nondirected C–H Alkylation DOI
Yogesh Bairagi,

Sandip Porey,

Sai V. C. Vummaleti

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(20), P. 15654 - 15664

Published: Oct. 7, 2024

β-Aryl ketones are essential structural units in natural products and bioactive molecules, commonly synthesized through coupling reactions involving prefunctionalized arenes or via directing group (DG) strategies. However, these conventional methods often inefficient, requiring multiple synthetic steps that escalate both the cost complexity of process. The need for additional steps, such as installation subsequent removal, further compromises atom economy overall efficiency. Herein, we report a palladium(II)-catalyzed dual ligand-enabled nondirected C–H alkylation with arene heteroarene limiting reagent synthesis β-(hetero)aryl less chemical waste. combined influence 2-methyl quinoxaline N-acetyl phenylalanine ligands imparts significant surge selectivity, facilitating diversification drugs alkylation. Integrated experimental computational mechanistic studies demonstrate activation regio- rate-determining step. Interestingly, while Pd–Ag heterobimetallic species is not directly involved 1,2-migratory insertion step, it proposed to play vital role during product release phase catalytic cycle.

Language: Английский

Citations

2
Palladium-Catalyzed Synthesis of α-Fluoro Olefins via C–H/C–F Coupling DOI
Mark Lautens, Colton E. Johnson

Synfacts, Journal Year: 2023, Volume and Issue: 20(01), P. 0047 - 0047

Published: Dec. 8, 2023

Key words palladium catalysis - defluorination C–H activation DFT calculations

Language: Английский

Citations

0