Light-Initiated Four-Step Domino-Multicomponent Synthesis of Functionalized Alkylidenecyclobutanes DOI

Xiaodan Yu,

Arthur Desvals,

Zong Chang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9915 - 9919

Published: Nov. 12, 2024

A four-step domino-multicomponent reaction (domino-MCR) is described for the synthesis of functionalized E-alkylidenecyclobutanes from 4-hydroxy-2-methylcyclopent-2-enone derivatives and three other simple reagents. The domino-MCR accomplished in a single protocol, comprising tandem photochemical [2 + 2]-cycloaddition/Norrish-I/γ-H transfer followed by an acetal protection allylic substitution reaction. In parallel, consecutive process has been established with distinct nonradiative sequences. An intramolecular version these reactions provides access to complex fused-bicyclic alkylidenecyclobutanes.

Language: Английский

Photoinduced C(sp3)−H Bicyclopentylation Enabled by an Electron Donor–Acceptor Complex‐Mediated Chemoselective Three‐Component Radical Relay DOI

Xiaobo Dang,

Zhixuan Li,

Jinlong Shang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: April 10, 2024

The photoredox electron donor-acceptor (EDA) complex-mediated radical coupling reaction has gained prominence in the field of organic synthesis, finding widespread application two-component reactions. However, EDA complex-promoted multi-component reactions are not well developed with only a limited number examples have been reported. Herein, we report photoinduced and highly chemoselective three-component arylalkylation [1.1.1]propellane, which allows direct functionalization C(sp

Language: Английский

Citations

11
Seven-membered N-heterocycles as approved drugs and promising leads in medicinal chemistry as well as the metal-free domino access to their scaffolds DOI Creative Commons
Aleksandra Leśniewska, Piotr Przybylski

European Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 275, P. 116556 - 116556

Published: June 5, 2024

Azepanes or azepines are structural motifs of many drugs, drug candidates and evaluated lead compounds. Even though compounds having N-heterocyclic 7-membered rings often found in nature (e.g. alkaloids), the natural this group rather rare as approved therapeutics. Thus, recently studied azepane azepine-congeners predominantly consist semi-synthetically synthetically-obtained scaffolds. In review a comparison drugs investigated leads was proposed taking into regard their aspects (stereochemistry), biological activities, pharmacokinetic properties confirmed molecular targets. The N-heterocycles reveal wide range not only against CNS diseases, but also e.g. antibacterial, anticancer, antiviral, antiparasitic allergy agents. As most potential structures, belonging to N-heterocycles, synthetic scaffolds, report reveals different efficient metal-free cascade approaches useful synthesize both simple azepine-containing congeners those oligocyclic structures. Stereochemistry azepane/azepine fused systems, view data binding with targets, is discussed. Apart from we compare advances SAR studies (mainly 2018 2023), whereas related part concerning various domino strategies focused on last ten years.

Language: Английский

Citations

11
Visible Light-Induced Radical Cascade Functionalization of Quinoxalin-2(1H)-ones: Three-Component 1,2-Di(hetero)arylation Approach with Styrenes and Thianthrenium Salts DOI

Sudip Sau,

Shinobu Takizawa, Hun Young Kim

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8821 - 8826

Published: Oct. 9, 2024

The additive-free visible light-induced three-component 1,2-di(hetero)arylation of styrenes was developed using quinoxalin-2(1

Language: Английский

Citations

4
Photoinduced C(sp3)−H Bicyclopentylation Enabled by an Electron Donor–Acceptor Complex‐Mediated Chemoselective Three‐Component Radical Relay DOI

Xiaobo Dang,

Zhixuan Li,

Jinlong Shang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(39)

Published: April 10, 2024

Abstract The photoredox electron donor–acceptor (EDA) complex‐mediated radical coupling reaction has gained prominence in the field of organic synthesis, finding widespread application two‐component reactions. However, EDA complex‐promoted multi‐component reactions are not well developed with only a limited number examples have been reported. Herein, we report photoinduced and highly chemoselective three‐component arylalkylation [1.1.1]propellane, which allows direct functionalization C(sp 3 )−H bicyclo[1.1.1]pentanes (BCP)‐aryl groups under mild conditions. A variety unnatural α‐amino acids, featuring structurally diversified 1,3‐disubstituted BCP moieties, were synthesized single‐step process. Notably, leveraging high tension release unstable transient aryl undergoes rapid conversion into relatively stable tertiary alkyl radical, consequently, competing side‐reaction was entirely suppressed. strategic use this approach would be useful for design diverse It is noteworthy that late‐stage incorporation pharmacophores peptides achieved both liquid‐phase solid‐phase This advancement anticipated to significant potential future development peptide drugs.

Language: Английский

Citations

3
Photocatalytic Enantioselective Radical Cascade Multicomponent Minisci Reaction of β‐Carbolines Using Diazo Compounds as Radical Precursors DOI Creative Commons
Yi‐Jie Gu, Mupeng Luo, Hua Yuan

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(25)

Published: April 19, 2024

Abstract Here, a photocatalytic asymmetric multicomponent cascade Minisci reaction of β‐carbolines with enamides and diazo compounds is reported, enabling an effective enantioselective radical C─H functionalization high yields enantioselectivity (up to 83% yield 95% ee). This protocol exhibits step economy, chemo‐/enantio‐selective control, good functional group tolerance, allowing access variety valuable chiral β‐carbolines. Notably, are suitable precursors in reactions. Moreover, the efficiency practicality this approach demonstrated by synthesis bioactive natural products.

Language: Английский

Citations

3
A new dual nickel/ferrocenyl-chalcone as photoredox catalyst along with DFT studies for the three-component domino performance DOI
Mohammad Bashiri, Mona Hosseini‐Sarvari, Sara Fakhraee

et al.

Journal of Photochemistry and Photobiology A Chemistry, Journal Year: 2024, Volume and Issue: 451, P. 115494 - 115494

Published: Jan. 28, 2024

Language: Английский

Citations

3
Photo(Multicomponent) Reaction of Quinoxalin‐2(1H)‐ones with CBrCl3 and Styrenes by Mes‐Acr‐MeClO4 DOI

Buddhadeb Pal,

Soumyashree Priyadarshinee,

Prasenjit Mal

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract In this study, we explored the use of Mes‐Acr‐MeClO 4 as a visible light photocatalyst for multicomponent reactions involving quinoxalin‐2( 1 H)‐ones with CBrCl 3 and styrene. The method showcases regioselective functionalization in three‐component system, forming two C─C bonds one pot. Mechanistic investigations suggest radical‐mediated pathway, initiated by photoexcitation , followed halogen atom abstraction from . This approach provides versatile sustainable route H)‐one functionalization, effectively facilitating photocatalyzed reaction under mild conditions irradiation, yielding high selectivity efficiency.

Language: Английский

Citations

1
Visible Light-Mediated Four-Component synthesis of Polyfunctionalized pyrroles using Eosin-Y via the HAT process DOI

Faezeh Ahmadi,

Monire Shariatipour, Masoumeh Jadidi Nejad

et al.

Journal of Photochemistry and Photobiology A Chemistry, Journal Year: 2024, Volume and Issue: 457, P. 115863 - 115863

Published: July 3, 2024

Language: Английский

Citations

0
Purple‐Light Promoted Thiol‐ene Reaction of Alkenes DOI Creative Commons
Polyssena Renzi, Marco Rusconi, Giovanni Ghigo

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4623 - 4633

Published: Nov. 2, 2023

Abstract Here we present a catalyst‐free protocol for the purple light‐mediated anti ‐Markovnikov functionalization of alkenes with thiols. Crucial to generation thiyl radical was formation key photo‐active complex. More than 30 thioether products were obtained, demonstrating tolerance towards different functional groups and scalability up 5 mmol alkene. Two reaction conditions have been developed, varying both solvent amount thiol. Depending on alkene structure, water can be used as an alternative dichloromethane solvent, thus increasing sustainability whole process.

Language: Английский

Citations

1
Light-Initiated Four-Step Domino-Multicomponent Synthesis of Functionalized Alkylidenecyclobutanes DOI

Xiaodan Yu,

Arthur Desvals,

Zong Chang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9915 - 9919

Published: Nov. 12, 2024

A four-step domino-multicomponent reaction (domino-MCR) is described for the synthesis of functionalized E-alkylidenecyclobutanes from 4-hydroxy-2-methylcyclopent-2-enone derivatives and three other simple reagents. The domino-MCR accomplished in a single protocol, comprising tandem photochemical [2 + 2]-cycloaddition/Norrish-I/γ-H transfer followed by an acetal protection allylic substitution reaction. In parallel, consecutive process has been established with distinct nonradiative sequences. An intramolecular version these reactions provides access to complex fused-bicyclic alkylidenecyclobutanes.

Language: Английский

Citations

0