Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(10), P. 2232 - 2235
Published: Jan. 1, 2023
A direct, aerobic and visible light photocatalytic approach to synthesize 4-thiocyanated 5-hydroxy-1H-pyrazoles via cross-coupling of pyrazolin-5-ones with ammonium thiocyanate is described. Under redox-neutral metal-free conditions, a series could be easily efficiently obtained in good high yields by using low-toxicity inexpensive as the source.
Language: Английский
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(38)
Published: July 31, 2023
Abstract Decarboxylative halogenation reactions of alkyl carboxylic acids are highly valuable for the synthesis structurally diverse halides. However, many reported protocols rely on stoichiometric strong oxidants or electrophilic halogenating agents. Herein, we describe visible‐light photoredox‐catalyzed decarboxylative N ‐hydroxyphthalimide‐activated that avoid and use inexpensive inorganic halide salts as Bromination with lithium bromide proceeds under simple, transition‐metal‐free conditions using an organic photoredox catalyst no other additives, whereas dual photoredox‐copper catalysis is required chlorination chloride. The mild display excellent functional‐group tolerance, which demonstrated through transformation a range complex acid containing natural products into corresponding bromides chlorides. In addition, show generality photoredox‐copper‐catalyzed functionalization by extension to thiocyanation potassium thiocyanide, was applied thiocyanates.
Language: Английский
Citations
25
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 4847 - 4855
Published: March 16, 2024
We disclose a copper-photocatalyzed strategy that enables selective access to organic thiocyanates and isothiocyanates using benzylic as ATRA reagents. The electronic nature of the aromatic system is crucial factor defining outcome reaction for forging either kinetic C–S or thermodynamic C–N bonds. Mechanistic investigations support radical pathway initiated by reductive bond cleavage substrates followed divergent inner-/outer-sphere interaction with copper depending on density formed intermediates. developed protocol proceeds high regio- chemoselectivity can also be applied late-stage functionalization bioactive molecules. utility products highlighted their facile conversion several building blocks are relevant synthesis.
Language: Английский
Citations
7
Tetrahedron Letters, Journal Year: 2025, Volume and Issue: 160, P. 155545 - 155545
Published: March 15, 2025
Language: Английский
Citations
1
Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(8)
Published: June 15, 2022
Abstract The incorporation of the cyanato‐chalcogen group (OCN, SCN, and SeCN) has piqued interest many researchers in field modern organic synthetic chemistry. Methodologies for selenocyanation are far less advanced than those OCN SCN chemistry due to scarcity SeCN transfer reagents approaches. It also been discovered that selenocyanate precursor (SeCN) performs significantly better thiocyanate (SCN) terms pharmacological properties scaffolds. Recent years, new (nucleophilic, electrophilic, radical) techniques were introduced allowed creation selenocyanato uncomplicatedly under gentle reaction conditions, particularly transition metal catalysis photo‐/electro‐chemically influenced reactions, which seemingly unimaginable. In this review, we have categorized a variety using various types regents their applications last decades, focusing on multiple catalysts preparation selenocyanates derivatives.
Language: Английский
Citations
24
Molecules, Journal Year: 2022, Volume and Issue: 27(11), P. 3461 - 3461
Published: May 27, 2022
Imidazopyridines constitute one of the most important scaffolds in medicinal chemistry, as their skeleton could be found a myriad biologically active molecules. Although numerous strategies were elaborated for imidazopyridine preparation 2010s, novel eco-compatible synthetic approaches have emerged, conscious climate change concerns. In this framework, photochemical methods been promoted to conceive heterocyclic motif over last decade. This review covers recently published works on synthesizing highly functionalized imidazopyridines by light induction.
Language: Английский
Citations
22
Organic Letters, Journal Year: 2022, Volume and Issue: 24(40), P. 7366 - 7371
Published: Oct. 4, 2022
Photoinduced benzylic C–H thiocyanation is described. A series of alkyl thiocyanates were efficiently obtained by using Selectfluor as the oxidant. Moreover, we accomplished one-pot isothiocyanation following thiocyanation. The and isothiocyanates applied to divergent transformation pharmaceuticals.
Language: Английский
Citations
20
Green Chemistry, Journal Year: 2023, Volume and Issue: 25(19), P. 7774 - 7781
Published: Jan. 1, 2023
Electrochemical cascade sequences for regioselective direct C7-thiocyanation of quinoxalin-2(1 H )-ones with ammonium thiocyanate have been developed.
Language: Английский
Citations
12
Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(4), P. 645 - 681
Published: Dec. 23, 2023
Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C-H bonds has evolved as a step- atom-economical method for the synthesis chalcogen-bearing compounds. Nevertheless, direct severely lags behind C-C, C-N C-O bond formations. Moreover, compared with monochalcogenation, reports selective mono-/dichalcogenation exclusive dichalcogenation relatively scarce. The past decade witnessed significant advancements various C(sp
Language: Английский
Citations
11
Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(9)
Published: Feb. 29, 2024
Abstract In light of the important biological activities and widespread applications organic disulfides, dithiocarbamates, xanthates, thiocarbamates thiocarbonates, continual persuit efficient methods for their synthesis remains crucial. Traditionally, preparation such compounds heavily relied on intricate multi‐step syntheses use highly prefunctionalized starting materials. Over past two decades, direct sulfuration C−H bonds has evolved into a straightforward, atom‐ step‐economical method organosulfur compounds. This review aims to provide an up‐to‐date discussion disulfuration, dithiocarbamation, xanthylation, thiocarbamation thiocarbonation, with special focus describing scopes mechanistic aspects. Moreover, synthetic limitations some these methodologies, along key unsolved challenges be addressed in future are also discussed. The majority examples covered this accomplished via metal‐free, photochemical or electrochemical approaches, which alignment overraching objectives green sustainable chemistry. comprehensive consolidate recent advancements, providing valuable insights dynamic landscape strategies crucial classes
Language: Английский
Citations
4
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(11), P. 1782 - 1787
Published: May 11, 2023
Abstract An electrochemical method for the C( sp 2 )−H thiocyanation of pyrazol‐5‐amines and enamines were developed in an undivided cell. A variety thiocyanated pyrazol‐5‐amine enamine derivatives accessed 36–91% yields, employing thiocyanate salts as electrolyte thiocyanating reagent. Moreover, this protocol can be extended to synthesis various iodinated brominated 51–95% yields. This does not require a metal or external chemical oxidants tolerates unprotected amino groups.
Language: Английский
Citations
9