Chemical Communications, Journal Year: 2022, Volume and Issue: 58(69), P. 9674 - 9677
Published: Jan. 1, 2022
An unprecedented, straightforward photochemical platform for efficient site-selective C–H alkylation of the C-7 position coumarins has been reported.
Language: Английский
Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(5), P. 1485 - 1507
Published: Jan. 1, 2022
Visible light and photoredox catalysis have emerged as a powerful long-lasting tool for organic synthesis, demonstrating the importance of variety chemical bond formation methods.
Language: Английский
Citations
84
Green Chemistry, Journal Year: 2023, Volume and Issue: 25(21), P. 8459 - 8493
Published: Jan. 1, 2023
This review comprehensively summarizes visible light-induced difunctionalization strategies for alkene and alkyne systems in metal-free conditions with literature coverage up to July 2023.
Language: Английский
Citations
40
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1719 - 1737
Published: Feb. 29, 2024
Abstract Aryl halides are one of the most important chemical feedstocks in pharmaceuticals due to its easy accessibility, inexpensiveness, and widely utilized as aryl radical precursors organic synthetic chemistry. Conventionally, stoichiometric reagents such AIBN/n‐Bu 3 SnH were used for generation from halides, suffered requirement toxic initiators, high temperature thus, development simple, mild strategies highly desirable. Recently, visible light mediated received considerable attention, allowing under reaction conditions. The present review described recent breakthroughs advancements photocatalyst‐free C−B/C/O/P/Se/S bond formation halides.
Language: Английский
Citations
14
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(17), P. 2818 - 2849
Published: July 7, 2023
Abstract In the last fifteen years, development of visible‐light photocatalysis, metal/photoredox dual catalysis has become forefront as a new paradigm in organic synthesis well carbohydrate chemistry. It led to discovery unprecedented transformations and also improvement known reactions under mild conditions, employing simple household light sources bench‐stable precursors, which meet requirements green chemistry sustainable excellent yield stereocontrol. general sense, exploitation photoredox hinges on capability photocatalyst or redox mediator transform visible into chemical energy via photo‐irradiated SET (single electron transfer), PET (photoinduced HAT (hydrogen atom XAT (halogen transfer) potentially unlock unique reaction pathways, thereby generating diverse array reactive intermediates. view type, mechanism, status, this review will systematically summarize latest advances visible‐light‐promoted photocatalytic glycosylation reactions, are driven by single photoactivity donor‐acceptor (EDA) complexes.
Language: Английский
Citations
19
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1784 - 1796
Published: Jan. 12, 2024
The atom transfer radical addition (ATRA) reaction is defined as a method for introducing halogenated compounds into alkenes via mechanism. In this study, we present an ATRA approach achieving regioselective functionalization of quinoxalin-2(1H)-ones by activating C–Br bonds CBr4 and subsequent trihaloalkyl-carbofunctionalization styrenes employing the 9-mesityl-10-methylacridinium perchlorate (Fukuzumi) photocatalyst under 3W blue LED (450–470 nm) irradiation. This three-component cascade process demonstrates remarkable efficiency in synthesis 1-methyl-3-(3,3,3-tribromo-1-(4-chlorophenyl)propyl)quinoxalin-2(1H)-one derivatives.
Language: Английский
Citations
6
Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(20), P. 5651 - 5667
Published: Jan. 1, 2021
This review summarizes the visible light mediated strategies for functionalization of allenes.
Language: Английский
Citations
36
Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(14), P. 2289 - 2306
Published: June 1, 2022
Abstract Heterocyclic N ‐oxides are prevalent in numerous natural products with broad applications pharmaceuticals, agrochemicals, material sciences, and asymmetric synthesis. Owing to their profound biological physiological activity unique chemical reactivity, the importance of these compounds has stimulated substantial interest among organic synthetic chemists. More importantly, C‐2 functionalization heterocyclic ‐oxides, including pyridine‐, isoquinoline‐, pyrazine‐, quinoxaline‐, quinoline is most important strategies for functionalization. Besides, deoxygenation also emerged as a reaction significance chemistry. In past decade, visible light photoredox catalyzed have drawn attention owing mild conditions. This review been categorized based on visible‐light‐mediated nondeoxygenative (alkylation, fluoroalkylation, arylation, acylation, amination), deoxygenative (sulfonylation, alkynylation, alkylation, acylation), (without C−H functionalization) ‐oxides. For part work, substrate scope, limitation, mechanism reactions discussed. magnified image
Language: Английский
Citations
26
ChemCatChem, Journal Year: 2022, Volume and Issue: 14(14)
Published: May 2, 2022
Abstract The 1, n ‐enynes are potent scaffolds in organic synthesis, providing a state‐of‐the‐art approach for synthesizing various acyclic and carbo‐ heterocyclic compounds. Radical cascade cyclization C−H functionalization of have gained immense attention the synthetic community. Significant advancement this field has been developed over years, employing harsh expensive metal catalysts usually associated with intense product purification unwanted side‐products. In context, advent visible light photocatalysis as mild efficient area is welcome step. Herein, we provide an exclusive overview recent developments light‐assisted manipulation ‐enynes. We classified review into 1,3‐, 1,4‐, 1,5‐, 1,6‐, 1,7‐, 1,8‐enynes, well dienyne, enediyne‐based reactions.
Language: Английский
Citations
23
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 10096 - 10110
Published: July 3, 2023
Herein we report a cascaded chalcogenation of aryl alkynoates or N-arylpropynamides using 9-mesityl-10-methylacridinium perchlorate as visible light photocatalyst to obtain selectively either 3-sulfenylated/selenylated coumarins spiro[4,5]trienones. In radical initiated process, the spiro-cyclization reaction was favored due presence -OMe -F substituent at para position group, which helped stabilize allylic intermediate formed during reaction. Otherwise, 6-endo-trig cyclization led coumarins. Overall, new C–S/C–Se, C–C, and C═O bonds were in single step. The Stern–Volmer quenching study, EPR experiments, ON-OFF trapping etc., understand radical-based mechanism.
Language: Английский
Citations
15
Organic Letters, Journal Year: 2021, Volume and Issue: 23(16), P. 6455 - 6460
Published: Aug. 3, 2021
A DBU-mediated cascade strategy of propargylamines with dimethyl 3-oxoglutarate for constructing a functionalized benzo[c]chromen-6-one core has been achieved. This process presumably involves sequence 1,4-conjugate addition, followed by lactonization, alkyne–allene isomerization, enol–keto tautomerization, 6π-electrocyclization, and aromatization. protocol features mild reaction conditions, simple operation, rich structural diversity, good functional group tolerance. photophysical survey reveals that the products exhibit fluorescence properties show potential exploring fluorescent material applications.
Language: Английский
Citations
25