Diastereoselective Trapping of Transient Carboxylic Oxonium Ylides with α,β‐Unsaturated 2‐Acyl Imidazoles

2020 ◽  
Vol 362 (21) ◽  
pp. 4662-4667
Author(s):  
Mengchu Zhang ◽  
Tianyuan Zhang ◽  
Dan Zhang ◽  
Wenhao Hu
Keyword(s):  
Oxonium Ylides

What role do oxonium ions and oxonium ylides play in the ZSM-5 catalysed methanol-to-olefin process?

2006 ◽  
Vol 417 (4-6) ◽  
pp. 309-315 ◽  
Author(s):  
D. Lesthaeghe ◽  
V. Van Speybroeck ◽  
G.B. Marin ◽  
M. Waroquier
Keyword(s):  
Oxonium Ions ◽  
Methanol To Olefin ◽  
Oxonium Ylides

Construction of Fused Medium-Ring Carbocycles by Catalytic Generation and Rearrangement of Oxonium Ylides

2006 ◽  
Vol 2006 (2) ◽  
pp. 323-327 ◽  
Author(s):  
J. Stephen Clark ◽  
Steven B. Walls ◽  
Claire Wilson ◽  
Stephen P. East ◽  
Martin J. Drysdale
Keyword(s):  
Oxonium Ylides ◽  
Medium Ring

The Stevens [1,2]-shift of oxonium ylides: a route to substituted tetrahydrofuranones

1992 ◽  
Vol 57 (12) ◽  
pp. 3479-3482 ◽  
Author(s):  
T. H. Eberlein ◽  
F. G. West ◽  
R. W. Tester
Keyword(s):  
Oxonium Ylides

Gold-Catalyzed Rearrangement of Allylic Oxonium Ylides: Efficient Synthesis of Highly Functionalized Dihydrofuran-3-ones

2013 ◽  
Vol 125 (15) ◽  
pp. 4292-4296 ◽  
Author(s):  
Junkai Fu ◽  
Hai Shang ◽  
Zhaofeng Wang ◽  
Le Chang ◽  
Wenbing Shao ◽  
...  
Keyword(s):  
Efficient Synthesis ◽  
Oxonium Ylides

Diazocarbonyl Compounds in Organofluorine Chemistry

Synlett ◽  
2020 ◽  
Author(s):  
Kálmán J. Szabó ◽  
Marvin Lübcke
Keyword(s):  
Density Functional ◽  
Functional Theory ◽  
Rhodium Catalysis ◽  
Dft Modeling ◽  
Modeling Studies ◽  
Oxonium Ylides ◽  
Electrophilic Reagents ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Labeling Method

AbstractDiazocarbonyl compounds are useful substrates in di- and trifunctionalization reactions based on F/CF3/SCF3 introduction. In the presented reactions, various electrophilic F/CF3/SCF3-transfer reagents were used. The majority of the reactions were based on rhodium catalysis and the application of various oxygen nucleophiles, such as alcohols, cyclic/acyclic ethers, and carboxylic acids. The oxyfluorination reactions were further developed to provide a new fluorine-18 labeling method. Density functional theory (DFT) modeling studies were performed to get a deeper mechanistic understanding of these reactions. These DFT modeling studies indicated that the catalytic reactions proceed through formation of rhodium carbene and oxonium ylide intermediates. The oxonium ylides undergo tautomerization to enol ether type species that subsequently react with the electrophilic F/CF3/SCF3-transfer reagents. We also present an arylation–trifluoromethylthiolation reaction for simultaneous introduction of C–SCF3 and C–C bonds into diazocarbonyl compounds. This reaction does not proceed by rhodium catalysis, but follows a Hooz-type mechanism.1 Introduction2 Diazocarbonyl Compounds: Versatile Substrates in Organic ­Synthesis3 Fluorination, Trifluoromethylation, and Trifluoromethylthiolation of Diazo Substrates3.1 Metal-Free Reactions3.2 Metal-Catalyzed Reactions with Nucleophilic Reagents3.3 Metal-Catalyzed Reactions with Electrophilic Reagents4 Oxyfluorination Reactions4.1 Fluorobenziodoxole as a Fluorine Source4.2 [18F]Fluorobenziodoxole as a Fluorine Source for Radiolabeling4.3 Oxyfluorination with NFSI5 Oxytrifluoromethylation6 Oxytrifluoromethylthiolation7 Arylation–Trifluoromethylthiolation Reaction8 Conclusions and Outlook

Fused vs. spiro: Kinetic, not thermodynamic preference may direct the reaction of α-carbonyl oxonium ylides

2019 ◽  
Vol 60 (24) ◽  
pp. 1582-1586 ◽  
Author(s):  
Natalia I. Guranova ◽  
Dmitry Dar'in ◽  
Grigory Kantin ◽  
Alexander S. Novikov ◽  
Olga Bakulina ◽  
...  
Keyword(s):  
Oxonium Ylides
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