1203-68-5Relevant academic research and scientific papers
Pinpoint-fluorinated phenanthrene synthesis based on C-F bond activation of difluoroalkenes Dedicated to Prof. Véronique Gouverneur on the occasion of her receipt of the 2014 ACS Award for Creative Work in Fluorine Chemistry.
Fuchibe, Kohei,Morikawa, Toshiyuki,Ueda, Ryu,Okauchi, Tatsuo,Ichikawa, Junji
, p. 106 - 115 (2015)
Treatment with a cationic palladium(II) catalyst promoted the Friedel-Crafts-type cyclization of 1,1-difluoro-1-alkenes bearing a biphenyl skeleton to afford regioselectively fluorinated (pinpoint-fluorinated) phenanthrenes via C-F bond activation. The obtained pinpoint-fluorinated phenanthrenes were observed to be organized by π-π and C-H?F interactions to exhibit columnar and layer structures in the solid state.
Annulation selectivity in the coupling of Fischer carbene complexes with o-alkynylbiphenyl and o-alkynylstyrene derivatives
Jackson, Thaddeus J,Herndon, James W
, p. 3859 - 3868 (2001)
The coupling of various Fischer carbene complexes with o-ethynylbiphenyl and an o-alkynylstyrene derivatives has been examined. In coupling reactions with methylcarbene and cyclopropylcarbene complexes, the major products are derived from C-H or C-C activation processes. In coupling reactions with phenylcarbene complexes, the major products are derived from the D?tz reaction.
Suzuki-Miyaura and Hiyama reactions catalyzed by orthopalladated triarylphosphite complexes
B?aszczyk, Izabela,Trzeciak, Anna M.
, p. 9502 - 9507 (2010)
Orthometallated, dimeric, and monomeric palladium complexes with triphenylphoshito ligands and square-planar complexes of the type PdCl 2[P(OR)3]2 (where R=Ph, m-MeC6H 4, o-MeC6H4, C6H3-2,4- tBu2) were applied in the Suzuki-Miyaura and the Hiyama reactions leading to the same product, 2-Mebiphenyl. The desired product was obtained in high yield in reactions performed in ethane-1,2-diol with Cs 2CO3 as a base. The optimized procedure was also applied to the synthesis of other biphenyl derivatives, and in most cases the Suzuki-Miyaura procedure led to higher yields of the product.
Macroporous resin impregnated palladium nanoparticles: Catalyst for a microwave-assisted green Hiyama reaction
Shah, Dipen,Kaur, Harjinder
, p. 69 - 73 (2012)
A non-functional macroporous commercial resin, Amberlite XAD-4, was impregnated with palladium nanoparticles of size 5-10 nm. The supported PdNPs, thus prepared, were used to catalyze the sodium hydroxide activated Hiyama cross-coupling reaction of phenyltrimethoxysilane with a variety of bromo and chloro arenes under microwave heating. They were found to have very high efficiency (TOF ≈ 3 × 104) and excellent recyclability. The procedure, which was carried out in the absence of any additional ligands, surfactants or toxic organic solvents, can lead to the development of a sustainable and green protocol for the production of biaryls.
Cu(OAc)2-catalyzed coupling of aromatic C-H bonds with arylboron reagents
Shang, Ming,Sun, Shang-Zheng,Dai, Hui-Xiong,Yu, Jin-Quan
, p. 5666 - 5669 (2014)
Cu-catalyzed coupling of aryl C-H bonds with arylboron reagents was accomplished using a readily removable directing group, which provides a useful method for the synthesis of biaryl compounds. The distinct transmetalation step in this Cu-catalyzed C-H coupling with aryl borons provides unique evidence for the formation of an aryl cupperate intermediate.
(Biphenyl-2-alkyne) derivatives as common precursors for the synthesis of 9-iodo-10-organochalcogen-phenanthrenes and 9-organochalcogen-phenanthrenes
Grimaldi, Tamiris B.,Lutz, Guilherme,Back, Davi F.,Zeni, Gilson
, p. 10415 - 10426 (2016)
In this paper, we report our results on the cyclization of (biphenyl-2-alkyne) derivatives to give two different types of phenanthrene derivatives, 9-iodo-10-organochalcogen-phenanthrenes and 9-organochalcogen-phenanthrenes. The strategy for the synthesis was based on the use of electrophilic cyclization for the preparation of 9-iodo-10-organochalcogen-phenanthrenes and iron(iii) chloride/diorganyl diselenide-mediated intramolecular cyclization to prepare 9-organochalcogen-phenanthrenes. The effects of solvent, temperature, reaction time and stoichiometry on the efficiency of cyclization reactions were investigated. The standard reaction conditions were compatible with many functional groups in the substrates, such as methyl, chlorine, fluorine and methoxyl. This protocol was efficient for diorganyl diselenides and disulfides but ineffective for diorganyl ditellurides. The resulting phenanthrenes were further functionalized through Sonogashira reactions followed by the electrophilic cyclization reaction to give the selenophene-fused aromatic compounds.
Palladium catalysed cross-coupling of aryl chlorides with arylboronic acids in the presence of a new tetraphosphine ligand
Feuerstein,Doucet,Santelli
, p. 1458 - 1460 (2001)
Cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclo pentane/[PdCl(C3H5)]2 system catalyses the cross-coupling of aryl chlorides with arylboronic acids with high ratios substrate/catalyst. A turnover number of 6800000 has been obtained for the addition of the activated 2-chloro-5-(trifluoromethyl)nitrobenzene to benzeneboronic acid in the presence of this catalyst.
PHOTODEGRADATION OF PHENANTHRENE IN THE PRESENCE OF HUMIC SUBSTANCES AND HYDROGEN PEROXIDE
Wang, C. X.,Yediler, A.,Peng, A.,Kettrup, A.
, p. 501 - 510 (1995)
The photodegradation of phenanthrene in water was investigated for a variety of reaction conditions employing various fulvic acids (FAs) as photosensitizers and hydrogen peroxide as oxidant. All experiments were conducted by using artificial sunlight from Suntest apparatus (Hanau, Germany) as light source. The relative rates of phenanthrene photodegradation for the different experimental conditions were computed. Fulvic acids of different origins influenced the rate of sunlight-induced photodegradation of phenanthrene in different ways. Hydrogen peroxide vigorously enhanced the photodegradation rate of phenanthrene. The photoproducts identified were oxygenated products of aromatic ring, such as 9,10-phenanthrenquinone, a group of hydroxyphenanthrene with hydroxyl at different position (1, 3, 4, and 9), 2,2'biphenyldicarbonic acid, 2,2'-biphenyldialdehyde and 2-phenylbenzaldehyde. It can be consumed that the phenanthrene photodegraded via free radical mechanism. - Keywords: Phenanthrene; Photodegradation; Fulvic Acids; Hydrogen Peroxide; Interaction
Restricted rotation in (phenylpyrrolidino)fullerene derivatives
Ajamaa, Fettah,Duarte, Teresa M. Figueira,Bourgogne, Cyril,Holler, Michel,Fowler, Patrick W.,Nierengarten, Jean-Francois
, p. 3766 - 3774 (2005)
A complete series of (phenylpyrrolidino)fullerene derivatives has been prepared. A detailed conformational analysis of these compounds has been carried out by variable-temperature 1H NMR experiments and computational studies. In the case of (phenylpyrrolidino)fullerene derivatives without ortho substituents, dynamic phenomena arising from restricted rotation around the phenyl-pyrrolidine bond are observed. In contrast, as soon as one of the ortho positions of the phenyl ring is substituted, the rotational energy barrier is high enough to prevent observation under our experimental conditions (room temperature to 120°C) of any dynamic exchange resulting from rotation of the phenyl substituent on the pyrrolidine ring. Whereas, in principle, two diastereoisomeric conformers can exist for the ortho-substituted (phenylpyrrolidino)fullerenes, only the atropisomers in which the unsubstituted ortho position is located atop the fullerene sphere are obtained. We conclude that the reaction of the ortho-substituted benzaldehyde derivatives with C 60 is diastereoselective, affording only one of the two possible atropisomers. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Convenient synthesis of palladium nanoparticles and catalysis of hiyama coupling reaction in water
Srimani, Dipankar,Sawoo, Sudeshna,Sarkar, Amitabha
, p. 3639 - 3642 (2007)
An efficient synthesis of Pd nanoparticles in water has been developed using a Fischer carbene complex of tungsten as the reductant and PEG as the capping agent. The colloidal palladium (1 mol %) efficiently catalyzes Hiyama cross-coupling reactions performed in air. Excellent yields of products were obtained with a wide range of substrates. Catalytic activity and stability of the nanoparticles were found to be inversely correlated.
