Photoredox-Catalyzed C–H Methylation of N-Heteroarenes Enabled by N,N-Dimethylethanolamine DOI
Jiayang Wang, Yun Wang, Wei-Yang Lin

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 21, 2024

A visible-light-driven radical C-H methylation of

Language: Английский

Syntheses, reactivity, and biological applications of coumarins DOI Creative Commons
Andrea Citarella, Serena Vittorio, Christian Dank

et al.

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 12

Published: Feb. 19, 2024

This comprehensive review, covering 2021-2023, explores the multifaceted chemical and pharmacological potential of coumarins, emphasizing their significance as versatile natural derivatives in medicinal chemistry. The synthesis functionalization coumarins have advanced with innovative strategies. enabled incorporation diverse functional fragments or construction supplementary cyclic architectures, thereby biological physico-chemical properties compounds obtained were enhanced. unique structure coumarine facilitates binding to various targets through hydrophobic interactions pi-stacking, hydrogen bonding, dipole-dipole interactions. Therefore, this important scaffold exhibits promising applications uncountable fields chemistry (e.g., neurodegenerative diseases, cancer, inflammation).

Language: Английский

Citations

18
Recent advances in catalytic decarboxylative transformations of carboxylic acid groups attached to a non-aromatic sp2or sp carbon DOI
Ajijur Rahaman,

Shivani Singh Chauhan,

Sukalyan Bhadra

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(28), P. 5691 - 5724

Published: Jan. 1, 2023

The current review highlights various decarboxylative transformations of α-keto acids, α,β-unsaturated acids and alkynoic developed since 2017.

Language: Английский

Citations

12
Photochemical radical decarboxylative disulfuration of α-keto acids and oxamic acids DOI
Huangbin Sun,

Xueting Bin,

Qianfang Zhang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(62), P. 8107 - 8110

Published: Jan. 1, 2024

A visible-light-induced directed decarboxylative disulfuration of α-keto acids and oxamic was developed. As a result, series versatile mono acyl disulfide derivatives synthesized under mild sustainable reaction conditions. This protocol has broad substrate scope, good functional-group tolerance, excellent synthetic applications.

Language: Английский

Citations

4
Photoinduced, Metal-Free Hydroacylation of Aromatic Alkynes for Synthesis of α,β-Unsaturated Ketones via C(sp3)–H Functionalization DOI
Ambuj Kumar Kushwaha, Arsala Kamal,

Himanshu Kumar Singh

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1416 - 1420

Published: Feb. 8, 2024

Despite the notable advancements made over past decade in achieving carbon–carbon bonds by transition-metal-catalyzed cross-coupling processes, metal-free reactions for hydroacylation of aromatic alkynes via C(sp3)–H functionalization are still rare and highly desired. Here we report a reliable approach synthesis α,β-unsaturated ketones (chalcones) using MeCN:H2O as green solvent, Eosin Y organic photocatalyst, ambient air oxidant. More significantly, this strategy can effectively transform variety methyl arenes into desired product. With high atom efficiency, use solvents, nature, environmental friendliness, visible light renewable energy source, method is compatible with biologically active molecules.

Language: Английский

Citations

3
Three-Component cine,ipso-Disubstitution of Nitrocoumarins DOI
Vincent Vedovato, Anghelo J. Gangano, Ion Ghiviriga

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(3), P. 647 - 652

Published: Jan. 12, 2024

The development of a three-component cine,ipso-disubstitution nitrocoumarins is reported. reaction leverages the electrophilicity nitrocoumarins, nucleophilicity nitronates, and leaving group ability nitrite (NO2–) to yield complex polyfunctionalized biaryls that often display stable axial chirality.

Language: Английский

Citations

1
Visible‐Light‐Induced Denitroalkylation of β‐Nitrostyrenes with Alkyl Boronic Acids DOI

Mingli Xu,

Chenyue Zhao,

Yongxiang Huang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 13(1)

Published: Nov. 22, 2023

Abstract Without an additional activator, the visible‐light‐catalyzed denitroalkylation of β ‐nitrostyrenes and alkyl boronic acids is reported. The efficient coupling cyclic secondary with various aryl nitroolefins realized, which gives olefins in 47–87 % yields. A possible mechanism involving fact that nitrite released from ‐nitrostyrene upon irradiation further activates to generate radicals proposed based on control experiments a literature survey.

Language: Английский

Citations

1
Copper-Catalyzed Synthesis of Difluoromethylated/C-4- and C-5-Functionalized Polycyclic Coumarin Derivatives DOI
Ziwei Li, Shuo Li,

Guosong Qian

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 8084 - 8098

Published: May 29, 2024

A facile and novel synthetic method for the synthesis of functionalized polycyclic coumarins at C-4 C-5 positions is proposed first time, which employs copper-catalyzed addition reactions undiscovered alkenes with difluoromethyl radicals to construct coumarins. This strategy characterized by high regioselectivity, easy availability raw materials, simple operation. Additionally, such coumarin can be reacted a variety precursors obtain wide range valuable position functionalized/difluoromethylated More importantly, some products showed significant inhibition proliferation in vitro against melanoma B16-F10 lung cancer A549 cell lines optimal IC

Language: Английский

Citations

0
Visible light–driven organic synthesis under ruthenium (RuII)-complex photocatalysis DOI
Goutam Brahmachari

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown, P. 151 - 219

Published: Aug. 16, 2024

Language: Английский

Citations

0
Substrate-controlled chemoselective assembly of coumarins and Morita–Baylis–Hillman alcohols from salicylaldehydes with acrylates DOI
Kai‐Kai Wang, Yanli Li, Can Wang

et al.

Synthetic Communications, Journal Year: 2024, Volume and Issue: 54(18), P. 1579 - 1588

Published: Aug. 27, 2024

Substrate-controlled divergent reactions of between salicylaldehydes and acrylates have been developed. By using methyl acrylate as the substrate with salicylaldehydes, a domino reaction was established, delivering coumarins good yield (up to 81% yields) high chemoselectivity under mild conditions. Whereas changed tert-butyl or iso-propyl acrylate, classical Morita − Baylis Hillman adducts were produced in yields 75% near exclusivity otherwise identical conditions, without any other competitive products. Additionally, synthetic utility present methodology further demonstrated by transformation. The structure typical product unambiguously established single crystal X-ray diffraction analysis.

Language: Английский

Citations

0
Visible-Light Photoredox-Catalyzed Direct Decarboxylative Functionalization of α-Keto Acids DOI
Huangbin Sun, Qianfan Zhang, Jie Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(20), P. 15225 - 15233

Published: Oct. 8, 2024

A novel and environmentally friendly photocatalytic strategy is presented for generating acyl radicals from benzoylformic acids, which are subsequently trapped by various sulfone-based SOMOphiles. This provides a robust toolkit to access variety of synthetically important functionalized aryl-ketone derivatives, efficiently directly construct acyl–S, acyl–Se, acyl–C, acyl–N bonds. The broad substrate scope, excellent functional group compatibility, mild reaction conditions make this protocol practical attractive.

Language: Английский

Citations

0