87682-44-8

Upstream product

• 573-17-1 9-bromophenanthrene 
• 536-74-3 phenylacetylene 
• 947-72-8 9-chlorophenanthrene 

Downstream Products

• 1107651-88-6 1-(phenanthren-9-yl)-2-phenylethane-1,2-dione 

Relevant academic research and scientific papers

Microwave-assisted Sonogashira cross-coupling reaction catalyzed by CN-ortho-palladated complex of tribenzylamine under copper-free conditions

Abstract The catalytic activity of [Pd{C6H4(CH2N(CH2Ph)2)} (μ-Br)]2 complex as an efficient, stable and non-sensitive to air and moisture catalyst was investigated in the Sonogashira cross-coupling reaction under microwave irradiation. In the presence of catalytic amount of this homogeneous catalytic system, various aryl halides were efficiently coupled with phenylacetylene under copper-free conditions. The substituted internal alkynes were produced in excellent yields in short reaction times in NMP at 100°. The combination of dimeric complex as homogenous catalyst and microwave irradiation and also NMP as microwave-active polar solvent gave higher yields in shorter reaction times.

Nano palladium supported on high-surface-area metal-organic framework MIL-101: An efficient catalyst for Sonogashira coupling of aryl and heteroaryl bromides with alkynes

Palladium nanoparticle-incorporated metal-organic framework MIL-101 (Pd/MIL-101) was successfully synthesized and characterized using X-ray diffraction, nitrogen physisorption, X-ray photoelectron, UV-visible and infrared spectroscopies, and transmission electron microscopy. The characterization techniques confirmed high porosity and high surface area of MIL-101 and high stability of nano-size palladium particles. Pd/MIL-101 nanocomposite was investigated for the Sonogashira cross-coupling reaction of aryl and heteroaryl bromides with various alkynes under copper-free conditions. The reusability of the catalyst was tested for up to four cycles without any significant loss in catalytic activity.

Copper(i) catalyzed Sonogashira reactions promoted by monobenzyl nicotinium chloride, a N-donor quaternary ammonium salt

A novel and effective catalytic system using monobenzylnicotinium chloride combined with copper(i) chloride was employed for the first time in Sonogashira cross-coupling reactions of phenylacetylene with various aryl halides. The goal was to use an efficient green media by using copper instead of palladium in metal-catalyzed coupling reactions. Monobenzyl nicotinium chloride, a quaternary ammonium salt containing a coordinating centre, plays an important role in this catalytic system and increases the efficiency of Cu(i) species during the reaction. A number of internal alkynes were produced in moderate to excellent yields in short reaction times in DMF at 135-140 °C. The efficiency of this catalytic system was compared with the copper-based catalyst obtained from dibenzylnicotinium chloride which has no N-donor active site, wherein lower activity was observed due to lack of a coordination site.

(BeDABCO)2Pd2Cl6 as an efficient homogeneous catalyst for copper-free Sonogashira cross-coupling reaction

An efficient catalytic system using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2] octane chloride and palladium chloride ((BeDABCO)2Pd 2Cl6) was developed for the Sonogashira reaction. In the presence of a catalytic amount of this efficient, stable homogeneous catalytic system that is non-sensitive to air and moisture, various aryl halides were efficiently coupled with phenylacetylene in good yields in H2O at 50C under copper-free conditions. Benzyl dabco as an efficient ligand and also a quaternary ammonium salt had an efficient stabilizing effect on the Pd(0) species. Copyright

Dimeric ortho-palladated homoveratrylamine as an efficient homogeneous catalyst for copper-free Sonogashira cross-coupling reaction

The catalytic activity of ortho-palladated [Pd{C6H2(CH2CH2NH2)-(OMe)2,3,4} (m-Br)]2, a complex of homoveratrylamine in the copper-free Sonogashira coupling reaction has been investigated. This complex is a catalyst that is efficient, stable and non-sensitive to air and moisture in the Sonogashira reaction. In this homogeneous catalytic system, various aryl halides were efficiently coupled with phenylacetylene in mostly moderate to good yields in N-methylpyrrolidone at 100 °C under copper-free conditions. Copyright

Transition-metal-free alkynylation of aryl chlorides

Two sets of conditions have been developed for a base-mediated, transition-metal-free alkynylation of aryl chlorides that proceeds via benzyne intermediates. The first set of conditions involves the use of TMPLi base in a pentane/THF mixture at 25 °C. The

The use of a bifunctional copper catalyst in the cross-coupling reactions of aryl and heteroaryl halides with terminal alkynes

Copper-catalyzed cross-coupling reactions of aryl halides and heteroaryl halides with terminal alkynes were carried out in DMF at 110-130 °C to provide the corresponding coupling products in satisfactory-to-good yields by using inexpensive 8-hydoxyquinoline as the ligand. Noteworthy is that the bifunctional copper catalyst was successfully applied in this alkynylation reaction for the first time. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Anomaly in Palladium-Catalyzed Phenylethynylation of 2,2'-Dihalobiphenyls: Formation of Alkylidenefluorenes

2,2'-Diiodobiphenyl and 5,5'-dinitro-2,2'-dihalobiphenyls underwent palladium-catalyzed phenylethynylation with 2 mol of phenylacetylene to yield 3-(fluoren-9-ylidene)-1,3-diphenylpropyne and 3-(3,6-dinitrofluoren-9-ylidene)-1,3-diphenylpropyne, respectively.These fluorenyl compounds exhibited well-defined splitting patterns for the fluorenyl ring protons in the 250-MHz proton NMR spectra.The structure of 3-(fluoren-9-ylidene)-1,3-diphenylpropyne was further confirmed by an independent synthesis via the thermolysis of diethyl 3-(fluoren-9-ylidene)-1,3-diphenylpropen-1-yl phosphate.The mechanistic importance of the complex iodo(fluoren-9-ylidenebenzyl)bis(triphenylphosphine)palladium(II) in the catalytic cycle was established on the basis of its reaction with phenylacetylene to give 3-(fluoren-9-ylidene)-1,3-diphenylpropyne.