Science China Chemistry, Journal Year: 2024, Volume and Issue: 68(5), P. 1717 - 1730
Published: Nov. 4, 2024
Language: Английский
Organometallics, Journal Year: 2024, Volume and Issue: unknown
Published: April 4, 2024
Many trifluoromethoxylation approaches often proposed nucleophilic AgIOCF3 as a key intermediate. However, the structure of this intermediate remains elusive. Herein, thermally stable, light-insensitive trifluoromethoxylating reagent [Ag(PPhtBu2)(OCF3)] (1) was prepared and fully characterized. Reagent 1 reacted with variety alkyl electrophiles including benzyl bromodes/chlorides, primary bromides/iodides/triflates/nosylates, secondary bromides/triflates/nosylates in good to excellent yields. Mechanistic investigation by reaction three enantioenriched suggested that these reactions proceed via an SN2 pathway, which is consistent our original mechanistic hypothesis.
Language: Английский
Citations
4
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(25)
Published: April 22, 2024
Abstract The fluoroalkoxy groups (OR f ) are widely used motifs in pharmaceutical and agrochemical fields due to their unique physicochemical properties including higher lipophilicity increased metabolic stability. Thus, the high value of OR ‐containing derivatives has stimulated development fluoroalkoxylation reactions. In this review, we highlight recent progress various trifluoroalkoxylating reagents applications organic synthesis past five years.
Language: Английский
Citations
4
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3179 - 3185
Published: Jan. 1, 2024
A deaminative functionalization of aliphatic tertiary amines via the cleavage C(sp 3 )–N bonds under transition metal-free conditions was disclosed, which goes through S N 2 reaction with various phosphorus and sulfur nucleophiles.
Language: Английский
Citations
3
Science Advances, Journal Year: 2025, Volume and Issue: 11(22)
Published: May 30, 2025
Indoles represent one of the most robust and synthetically versatile classes heteroaromatic compounds. However, stereoselective conversion planar indole rings into three-dimensional indoline skeletons bearing multiple stereogenic centers remains a persistent challenge in organic synthesis. Herein, we describe an intermolecular catalytic asymmetric dearomatization simple indoles via palladium-catalyzed three-component cross-coupling reaction. By using readily accessible diazonium salts aromatic boronic acids as arylative reagents under ligand-swap strategy, this method enables efficient construction 2,3-diarylated indolines. Mechanistic studies reveal that chiral BiOx ligand governs highly migratory insertion aryl-palladium intermediate indole’s C═C double bond with complete diastereo- regioselectivity, whereas achiral fumarate facilitates reductive elimination step, corroborated by density functional theory calculations. Furthermore, protocol is extended to dearomative diarylation benzofurans, affording 2,3-dihydrobenzofuran derivatives high stereocontrol.
Language: Английский
Citations
0
Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
A novel synthetic protocol for α-trifluoromethoxy sulfides through the Pummerer rearrangement was developed.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5856 - 5861
Published: July 1, 2024
Here, we present a silver-catalyzed decarboxylative nitrooxylation via radical-based approach. The substrate scope of this reaction prototype extends to nonactivated primary and secondary carboxylic acids. This protocol provides practical method for the synthesis an unprecedented family organic nitrates exhibits wide functional group compatibility. Preliminary mechanistic studies reveal that high-valent silver(II) nitrate complex is versatile NO
Language: Английский
Citations
1
Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7139 - 7143
Published: Aug. 15, 2024
We report an efficient perfluoroalkoxylation reaction of alkyl halides catalyzed by copper(I) iodide (CuI), which facilitates the simultaneous activation both perfluoroalkoxide and halides. This methodology is tolerant a wide range functional groups eliminates need for costly metal reagents. The conducted in single step under mildly practical conditions.
Language: Английский
Citations
1
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 15, 2024
Sulfation is a highly valuable pathological and physiological process, yet it often underappreciated considering the rather difficult accessibility of organosulfates. O-sulfonation (O-SO
Language: Английский
Citations
1
Letters in Organic Chemistry, Journal Year: 2024, Volume and Issue: 21(10), P. 898 - 908
Published: March 12, 2024
Abstract: In this study, the synthesis of N-alkyl-3-(indol-3-yl)pyrazoles was carried out from Ag2CO3 catalyzed regioselective aza-Michael addition 5-(indol-3-yl)-1H-pyrazoles to α, β-unsaturated carbonyl compounds. presence 10 mol% Ag2CO3, reaction smoothly occurred in dichloroethane (DCE) at 120°C preferentially afford a series high yields with good regioselectivity. It found that 1-methyl-3-(3-methyl-1H-pyrazol-5-yl)-2-phenyl- 1H-indole, 1-benzyl-3-(3-methyl-1H-pyrazol-5-yl)-1H-indole, ketone, and β- unsaturated amide exclusively gave 3-(pyrazol-3-yl)indoles yields. This features regioselectivity, mild conditions, substrate scope yields, commercially available catalyst. Meanwhile, also proven be quite practical by gram-scale excellent
Language: Английский
Citations
0
Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9764 - 9768
Published: Nov. 5, 2024
The first rhodium-catalyzed trifluoromethoxylation of allenylic trichloroacetimidates has been reported. products were obtained through a procedure using trifluoromethyl arylsulfonate (TFMS) as the trifluoromethoxy source with yield up to 76% by identifying ligand diene. reaction proceeds under mild conditions excellent functional group tolerance and complete regiocontrol.
Language: Английский
Citations
0