Using carboranes as counterions, fluorinated benzyl-type carbocations such as (p-FC(6)H(4))(2)CF(+), (p-FC(6)H(4))(CH(3))CF(+) and fluorinated trityl ions are readily isolated for X-ray and IR structural characterization.

The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepared from Pd(OCOCF3)2 and a chiral pyridinooxazoline ligand yields enantioenriched products bearing benzylic stereocenters. Notably, this t...

The diastereoselective synthesis of fluorinated δ-lactams has been achieved through an efficient five step process. The route can tolerate a range of functionalities, and provides a quick route for the generation of new fluorinated medicinal building blocks.

Introduction: Fluorine (F) magnetic resonance spectroscopy (MRS) can monitor the concentration and metabolism of fluorinated cancer drugs like 5-fluorouracil (5-FU) and its oral prodrug capecitabine in vivo [1]. Previous F MRS animal studies of capecitabine and 5-FU metabolism used a variety of anesthetic agents including injectable fluorinated compounds like Hypnovel and Hypnorm [2]. Fluorinat...

The effect of the curvature of the carbon lattice is discussed taking into account NMR data on various fluorinated carbons including C(60) fullerenes, single, double and multiwall carbon nanotubes. Graphite fluorides and highly fluorinated fullerenes are used as limit model compounds for planar and spherical geometries, respectively. The curvature results in a weakening of the C-F bonding coval...

Several fluorinated and trifluoromethylated indanone, tetralone and naphthone derivatives have been prepared via Claisen condensations and selective fluorinations in yields ranging from 22–60%. In addition, we report the synthesis of new, selectively fluorinated bindones in yields ranging from 72–92%. Of particular interest is the fluorination and trifluoroacetylation regiochemistry observed in...

Effect of electronegative substituents on ring opening of [2.2.2]propellane was examined by quantum chemical calculations at CASSCF and CASPT2 level of theory. Comparison of the results with those obtained with MR-AQCC calculations indicated that calculations beyond CASSCF level were needed for reliable description of the process. Calculations show a strong effect of fluorination on the central...

Despite the growing importance of fluorinated organic compounds in drug development, there are no direct protocols for the fluorination of aliphatic C-H bonds using conveniently handled fluoride salts. We have discovered that a manganese porphyrin complex catalyzes alkyl fluorination by fluoride ion under mild conditions in conjunction with stoichiometric oxidation by iodosylbenzene. Simple alk...

Metabolism of trans-7,8-dihydroxy-7,8-dihydro-6-fluorobenzo(a)pyrene by liver microsomes from 3-methylcholanthrene-treated rats and by a highly purified monooxygenase system, reconstituted with cytochrome P-450c, has been examined. Although both the fluorinated and unfluorinated 7,8-dihydrodiol formed from benzo(a)pyrene by liver microsomes share (R,R)-absolute configuration, the fluorinated di...