Synfacts, Journal Year: 2023, Volume and Issue: 20(01), P. 0077 - 0077
Published: Dec. 8, 2023
Key words photocatalysis - N-heterocyclic carbene amino esters imidyl radicals
Language: Английский
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(11), P. 8270 - 8293
Published: May 13, 2024
As one of the most important key intermediates, NHC-bound acylazolium-based ionic transformations have been intensively explored in past two decades. With expeditious development NHC-catalyzed radical recent years, acylazolium chemistry has reached another level, with number relevant publications increasing significantly. However, a summary focused on acylations NHC-derived acyl azoliums classified according to mechanistic difference not reported. Such detailed classification and deep analysis provide opportunities for better understanding history trend this field. In review, reactions N-heterocyclic carbene (NHC)-derived are systematically introduced. The achievements challenges within area also summarized discussed at end.
Language: Английский
Citations
23
Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 17, 2025
1,2-Amino-difunctionalization reactions of alkenes allow the efficient introduction different functional groups and rapid construction valuable functionalized amines. In this respect, we report a copper-catalyzed 1,2-amino-alkoxycarbonylation unactivated with CO alkylamine precursors in presence Lewis acid additive. The novel protocol allows direct access to β-amino derivatives from easily available starting materials. presented methods feature high chemo- regioselectivities, good group tolerance, substrate scope including diverse bioactive compounds drug-like molecules. Mechanistic studies indicate that additive is key realizing umpolung addition nucleophilic aminyl radicals electron-rich alkenes, which represents an elegant activation strategy for radicals.
Language: Английский
Citations
1
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(21), P. 14745 - 14753
Published: May 14, 2024
We herein describe a Ni-catalyzed formal hydroamidation of readily available α,β-unsaturated carbonyl compounds to afford valuable chiral β-amino acid derivatives (up >99:1 e.r.) using dioxazolones as robust amino source. A wide range alkyl-substituted olefins conjugated esters, amides, thioesters, and ketones were successfully amidated at the β-position with excellent enantioselectivity for first time. Combined experimental computational mechanistic studies supported our working hypothesis that this unconventional β-amidation unsaturated substrates can be attributed polar-matched migratory olefin insertion an (amido)(Cl)Ni
Language: Английский
Citations
6
Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)
Published: Oct. 16, 2024
The carboamination of unsaturated molecules using bifunctional reagents is considered an attractive approach for the synthesis nitrogen-containing compounds. However, C-N have never been employed in cyclopropane. In this study, we use N-heterocyclic carbene (NHC), N-benzoyl saccharin, as a reagent and photoredox catalyst dual-catalyzed 1,3-aminoacylation NHCs play multiple roles, functioning Lewis base catalysts to activate bonds, promoting oxidative quenching process PC*, acting efficient acyl radical transfer formation C-C bonds. between excited-state PC* NHC adduct key photooxidation generality aryl cyclopropanes.
Language: Английский
Citations
4
ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(2), P. 1287 - 1293
Published: Jan. 7, 2025
C(sp3)–H bond functionalization is a powerful strategy for the synthesis of organic compounds due their abundance in simple starting materials. Photoredox catalysis has led to diverse array enabling activation strategies; however, general platform direct carboxylic acid derivatives remains elusive. Disclosed herein development cooperative NHC/photoredox-catalyzed esterification transformation. This method enables access benzylic, α-heteroatom, and formal β-esterification products moderate high yields under mild reaction conditions.
Language: Английский
Citations
0
International Journal of Nanomedicine, Journal Year: 2025, Volume and Issue: Volume 20, P. 2395 - 2409
Published: Feb. 1, 2025
Hepatocellular carcinoma is one of the most challenging malignancies and has high incidence mortality rates worldwide. Digital subtraction angiography (DSA)-guided hepatic arterial infusion standard chemotherapeutic agent oxaliplatin (OXA) advantages both precision efficacy, making it an important therapeutic strategy for advanced-stage liver cancer. However, patients receiving this treatment still face severe systemic toxicity poor tolerability oxaliplatin. In study, we compared with novel albumin-formulated oncolytic peptide nanoparticles, Ir-cR8 (abbreviated as iPep), in orthotopic cancer a mouse model by intravenous injection rabbit via DSA-guided infusion. The results showed that Ir-cR8-BSA-NPs had enhanced inhibitory effects to growth H22 ectopic tumors mice also reduced animals OXA treatment. Specifically, Ir-cR8-BSA-NPs-treated approximately 92% tumor inhibition 88% OXA. VX2 hepatocellular model, demonstrated significantly stronger (P<0.01) size OXA, assessed PET/CT imaging, SUV values decreasing from 5.15±0.46 2.52±0.57, OXA-treated group, which decreased 5.44±0.43 3.90±0.24. Furthermore, Ir-cR8- BSA-NPs improved stability albumin encapsulation hemolytic (P<0.001), resulting efficacy. This study combined membrane-active nanomedicine precise drug delivery enabled technology interventional
Language: Английский
Citations
0
Molecules, Journal Year: 2024, Volume and Issue: 29(4), P. 790 - 790
Published: Feb. 8, 2024
Monofluoromethyl (CH2F) motifs exhibit unique bioactivities and are considered privileged units in drug discovery. The radical monofluoromethylative difunctionalization of alkenes stands out as an appealing approach to access CH2F-containing compounds. However, this strategy remains largely underdeveloped, particularly under metal-free conditions. In study, we report on visible light-mediated three-component monofluoromethylation/acylation styrene derivatives employing NHC organic photocatalyst dual catalysis. A diverse array α-aryl-β-monofluoromethyl ketones was successfully synthesized with excellent functional group tolerance selectivity. mild CH2F generation from NaSO2CFH2 holds potential for further applications fluoroalkyl chemistry.
Language: Английский
Citations
3
Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 23, 2024
Herein, we report a mild and operationally simple photoredox/NHC dual catalysis strategy for the α-carboxylation of tertiary amine C(sp
Language: Английский
Citations
3
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13085 - 13092
Published: Aug. 28, 2024
An amidoarylcarbonylation reaction of aromatic aldehydes and olefins with Katritzky pyridinium salts by N-heterocyclic carbene (NHC)-catalyzed radical relay to construct C-C C-N bonds good functional group tolerance is developed for the synthesis β-acylamino ketones. This gentle efficient approach offers a valuable style Mechanistic studies revealed that addition/coupling/elimination cascade process was involved in this reaction.
Language: Английский
Citations
2
Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8848 - 8853
Published: Oct. 8, 2024
A N-heterocyclic carbene-catalyzed (NHC) three-component reaction involving
Language: Английский
Citations
2