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PubMed2004

Selective and effective fluorination of organic compounds in water using Selectfluor F-TEDA-BF4.

[reaction: see text] Selective and effective fluorination of various types of organic compounds performed in water as the reaction medium using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor F-TEDA-BF4) is reported. 2-Naphthole and 2-methoxynaphthalene were thus transformed to 1,1-difluoro-2(1H)naphthalenone, estrone to 10beta-fluoro-1,4-estradien-3,17-dione, phenyl-substituted alkenes to vicinal fluorohydrins, and various ketones, 1,3-diketones, or beta-ketoesters to corresponding alpha-fluoro or alpha,alpha-difluoro ketones.

Journal Article↗
PubMed1999

Electrolytic Partial Fluorination of Organic Compounds. 30.(1) Drastic Improvement of Anodic Monofluorination of 2-Substituted 1,3-Oxathiolan-5-ones Using the Novel Fluorine Source Et(4)NF.4HF.

The highly regioselective anodic monofluorination of 2-substituted 1,3-oxathiolan-5-ones was successfully carried out using a novel supporting electrolyte, Et(4)NF.4HF, while use of a conventional supporting electrolyte, Et(3)N.3HF, resulted in no formation or extremely low yields of the fluorinated products.

Journal Article↗
PubMed2006

Cationic Rh(I) catalyst in fluorinated alcohol: mild intramolecular cycloaddition reactions of ester-tethered unsaturated compounds.

In fluorinated alcohols, the cationic Rh(I) species, which is derived from [Rh(COD)Cl]2 and AgSbF6, efficiently catalyzed intramolecular [4+2] cycloaddition reactions of ester-tethered 1,3-diene-8-yne derivatives. The catalytic system was also effective in intramolecular [5+2] cycloaddition reactions of ester-tethered omega-alkynyl vinylcyclopropane compounds.

Alcohols↗
PubMed2002

Electrolytic partial fluorination of organic compounds. 64.(1) Anodic mono- and difluorination of thiazolyl sulfides.

The anodic fluorination of 2-thiazolyl methyl sulfide, 2-thiazolyl propargyl sulfide, and 2-thiazolyl acetonyl sulfide was successfully carried out to provide the corresponding 5-fluorothiazole and 2,5,5-trifluorothiazoline derivatives. The latter products were readily hydrolyzed to give isolable 5,5-difluoro-2-hydroxythiazoline derivatives. On the other hand, anodic fluorination of 2-thiazolyl cyanomethyl sulfide afforded 5-fluorothiazole and alpha-fluorinated thiazole derivatives. Thus, the product selectivity was found to be greatly changed by the electron-withdrawing ability of substituents at the side chain of the thiazole ring. This is the first report of a successful anodic fluorination of a thiazole ring.

Journal Article↗
PubMed2004

Electrochemical partial fluorination of organic compounds. 74. Efficient anodic synthesis of 2-fluoro- and 2,3-difluoro-2,3-dihydrobenzofuran derivatives.

Anodic fluorination of 3-substituted benzofuran derivatives in a variety of fluoride salts resulted in the formation of three fluorinated products; two stereoisomers of 2,3-difluoro-2,3-dihydrobenzofuran (cis and trans) and cis-2-fluoro-3-hydroxy-2,3-dihydrobenzofuran derivatives. Dehydrofluorination of the main products, cis-difluoro derivatives, furnished the nonaromatic 2-fluoro-3-benzofuranyledene derivatives instead of the aromatic 2-fluorobenzofuran derivatives.

Journal Article↗
PubMed2001

Electrolytic partial fluorination of organic compounds. 54. Anodic mono- and trifluorination of thiochroman-4-one derivatives and the factors affecting product selectivity.

Anodic fluorination of (E)-3-benzylidene-2,3-dihydrothiochroman-4-one and 3-benzyl-1-thiochromone derivatives under a variety of electrolytic conditions was found to provide selectively or exclusively the same fluorinated products: (E)-3-benzylidene-2,3-dihydro-2-fluorothiochroman-4-ones. In addition, di- and trifluorinated derivatives were also obtained depending on the starting heterocycles and electrolytic conditions. The factors affecting the product selectivity were also examined.

Journal Article↗
PubMed2003

Synthesis, crystal structure, and characterization of the first Nb(3) triangular cluster compound bonded to fluorine ligands: association of Nb(3)I(i)F(i)(3)F(a)(8)L(a) units and Nb(IV)L(6) Octahedra with L=O and F.

The synthesis and the crystal structure of the first compound containing Nb(3) triangular clusters bonded to fluorine ligands are presented in this work. The structure of Nb(3)IF(7)L(NbL(2))(0.25) with L = O and F, determined by single-crystal X-ray diffraction, is based on a Nb(3)I(i)F(i)(3)F(a)(8)L(a) unit and a NbL(6) octahedron (tetragonal, space group I4/m, a = 13.8638(3) A, c = 8.9183(2) A, V = 1714.14(7) A(3), Z = 8). Two crystallographic positions (noted L5 and L6) are randomly occupied by fluorine and oxygen with two different F:O occupancies. These L ligands build an octahedral site for a single niobium atom, located between the units. The four L5 ligands of the NbL(6) octahedron are shared with four Nb(3) cluster units, while the two other L6 ligands are terminal. The Nb(3) cluster is face-capped by one iodine and edge-bridged by three fluorine ligands. Two of the three niobium atoms constituting the cluster are bonded to three additional apical fluorine ligands, while the third one is bonded to two fluorines and one L5 ligand. The Nb(3) cluster is linked to six adjacent ones via all the apical fluorine ligands. The developed formula of the unit is therefore Nb(3)I(i)F(i)(3)F(a)(-)(a)(8/2)L(a) according to the Schäfer and Schnering notation. The oxidation state of the single niobium and the random distribution of fluorine and oxygen on the two L sites will be discussed on the basis of structural analysis, the bond valence method, and IR and EPR measurements. The structural results will be compared to those of previously reported niobium compounds containing NbF(6) or Nb(F,O)(6) octahedra.

Journal Article↗
PubMed2000

Electrolytic partial fluorination of organic compounds. 42.(1) marked solvent effects on regioselective anodic monofluorination of 4-oxo-2-pyrimidyl sulfides.

Regioselective anodic monofluorination of 4-oxo-2-pyrimidyl sulfides was investigated under various electrolytic conditions. Anodic fluorination was successfully carried out using Et(4)NF.4HF in dimethoxyethane (DME) to provide the corresponding alpha-fluorinated products in good yields. In contrast, acetonitrile (MeCN) was not suitable for the anodic fluorination due to the severe anode passivation during the electrolysis. A mixed solvent of DME and MeCN was found to be also effective for the fluorination, and the product yield increased with an increase of the ratio of DME to MeCN. The superiority of DME can be explained mainly in terms of the suppression of the anode passivation and enhancement of the nucleophilicity of the fluoride ions. Such marked solvent effects on the anodic fluorination were discussed in detail.

Journal Article↗