Synthesis and NMR studies of 2- and 3-fluorosubstitued five-membered heterocycles

  title={Synthesis and NMR studies of 2- and 3-fluorosubstitued five-membered heterocycles},
  author={Elena Dvornikova and Małgorzata Bechcicka and Krystyna Kamieńska‐Trela and Adam Kr{\'o}wczyński},
  journal={Journal of Fluorine Chemistry},
26 Citations

Efficient Preparation of 3-Fluoropyrrole Derivatives

Noble N-substituted-3-fluoropyrroles derivatives were prepared from new precursor via ring formation. The addition reaction of ethyl iododifluoroacetate to vinyl trimethylsilane under the Cu(0)

Indium-catalyzed C-F Bond Transformation through Oxymetalation/β-fluorine Elimination to Access Fluorinated Isocoumarins.

The indium-catalyzed C-F bond transformation of 2-(2,2-difluorovinyl) benzoates is reported, which is readily accessible compounds, to give a diverse array of fluorinated isocoumarins.

Fluorinated porphyrins and corroles: Synthesis, electrochemistry, and applications

Fluorination alters the electronic structure of aromatic systems in a predictable manner, and these effects can be exploited in the design of aromatic, macrocyclic ligand systems for a variety of

Gold(I)‐Catalyzed Cycloisomerization of 2‐Fluoroalk‐3‐yn‐1‐ones: Synthesis of 2,5‐Substituted 3‐Fluorofurans

Fluorination of 1,4-disubstituted tert-butyldimethylsilyl but-1-en-3-yn-1-yl ethers with Selectfluor gives 2-mono-fluorobut-3-yn-1-ones. Subsequent 5-endo-dig cyclization in the presence of

Microwave-assisted fluorination of 2-acylpyrroles: synthesis of fluorohymenidin.

Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position, which resulted in dihydrofluorohymenidin being synthesized and dehydrogenated to fluorohy menidin as the first fluorinated pyr role-imidazole alkaloid.

Convenient electrophilic fluorination of functionalized aryl and heteroaryl magnesium reagents.

Fluorine-substituted aromatic and heterocyclic compounds are important target molecules due their useful physical and biological properties. Fluorinated arenes and especially heteroarenes are

Synthesis of Halogenated 5- and 6-Membered Sulfur- and Sulfur, Nitrogen-Containing Heterocycles

This review describes the data concerning the chemistry of halogenated 5- and 6-membered sulfur- and sulfur, nitrogen-containing heterocycles published in literature since 2000. The only monocyclic

Synthesis of 2-aryl-3-fluoro-5-silylthiophenes via a cascade reactive sequence.

These transformations include the first successful S(N)2'-type reaction of 2-bromo-3,3, 3-trifluoropropene and benzylthiols and [2,3]sigmatropic rearrangement of 2,3-difluoroallyl benzyl sulfide.

Substituent effects on indirect carbon–carbon couplings, J(CC), in substituted thiophenes, pyrroles, and furans studied by experiment and theory

An excellent linear correlation is found between a large set of experimental spin–spin carbon–carbon coupling constants, J(CC), in thiophene, pyrrole, and furan systems and the corresponding



DFT–GIAO and DFT–NBO studies of the origin of 19F NMR shielding effects in alkyl fluorides

Electron delocalization into the local environment of the fluorine nucleus in the anti (1) and syn (2) epimers of 7‐norbornenyl fluoride, 7‐fluoronorbornane (3), 7‐fluoronobornadiene (4) and the

Attempted syntheses of aminofluorothiophenes

It appeared that a key intermediate for 2-amino-3-fluorothiophene (1), methyl 3-fluorothiophene-2-carboxylate (5), had been prepared by a Schiemann reaction of the 3-diazonium salt (6) in xylenes.

1,3-Dipolar cycloaddition of azomethine ylides derived from imines and difluorocarbene to alkynes: a new active Pb-mediated approach to 2-fluoropyrrole derivatives

Domino reactions of imines with difluorocarbene in the presence of electron-deficient alkynes lead to 2-fluoropyrrole derivatives. The process involves intermediate azomethine ylide formation, its

19F NMR chemical shifts. 1. Aliphatic fluorides.

The fluorine shielding in the series of fluoromethanes also decreases with increasing fluorine substitution, and the decreased shielding arises from the highest occupied MO, which is a nonbonding linear combination of pure p functions at the fluorines.

Preparative polar organometallic chemistry

I. Reactivity of Polar Organometallic Intermediates.- 1 Introduction.- 2 Alkylation.- 2.1 Reactivity-A Qualitative Comparison of the Polar Organometallics.- 2.2 Scope of the Alkylation Reaction.- 2.3