862996-06-3Relevant articles and documents
Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand
Song, Chun,Ma, Yudao,Chai, Qiang,Ma, Chanqin,Jiang, Wei,Andrus, Merritt B.
, p. 7438 - 7446 (2005)
A novel bis-phenanthryl N-heterocyclic carbene (NHC) based palladium acetate catalyst was effective for the coupling of various aryl and vinyl chlorides with organoboron compounds. N,N-Bis-(2,9-dicyclohexyl-10-phenanthryl)- 4,5-dihydroimidazolium chloride 8 (H2ICP·HCl) with Pd(OAc)2 and KF·18-c-6 in THF at room temperature gave Suzuki-Miyaura coupling of aryl and vinyl chorides, including unactivated and di-ortho substituted substrates in high yields. Hindered tri- and tetra-ortho substituted products were also efficiently produced. Benzyl chloride was also found to be a useful coupling partner and trimethylboroxine was used to give methylated products. The effect of ligand, base, temperature, solvent, and reaction time are reported along with various substrates including halides and triflates.
Chiral Dinuclear Vanadium Complex-Mediated Oxidative Coupling of Resorcinols
Sako, Makoto,Aoki, Takanori,Zumbr?gel, Nadine,Schober, Lukas,Gr?ger, Harald,Takizawa, Shinobu,Sasai, Hiroaki
, p. 1580 - 1587 (2019/02/08)
A method for the highly regio- and enantioselective oxidative coupling of resorcinols has been established by using dibrominated dinuclear vanadium(V) catalyst 1c under air. When resorcinols bearing an aryl substituent were applied as substrates to the co
[Pd(Cl)2(P(NC5H10)(C6H 11)2)2] - A highly effective and extremely versatile palladium-based negishi catalyst that efficiently and reliably operates at low catalyst loadings
Bolliger, Jeanne L.,Frech, Christian M.
experimental part, p. 11072 - 11081 (2010/11/16)
[Pd(Cl)2(P(NC5H10)-(C6H 11)2]2] (1) has been prepared in quantitative yield by reacting commercially available [Pd(cod)(Cl)2] (cod = cyclooctadiene) with readily prepared 1-(dicyclohexylphosphanyl)piperidine in toluene under N2 within a few minutes at room temperature. Complex 1 has proved to be an excellent Negishi catalyst, capable of quantitatively coupling a wide variety of electronically activated, non-activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100°C in the presence of just 0.01 mol% of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetais, lactones, amides, anilines, alkenes, carboxylic acids, acetic acids, and pyridines and pyrimidines, have been successfully used as coupling partners. Furthermore, electronic and steric variations are tolerated in both reaction partners. Experimental observations strongly indicate that a molecular mechanism is operative.
Structural modifications of the cannabinoid side chain towards C3-aryl and 1′,1′-cycloalkyl-1′-cyano cannabinoids
Papahatjis, Demetris P.,Nahmias, Victoria R.,Andreou, Thanos,Fan, Pusheng,Makriyannis, Alexandros
, p. 1616 - 1620 (2007/10/03)
The compounds reported in this study are Δ8-THC analogues in which the C3 five-carbon linear side chain of Δ8-THC was replaced with aryl and 1′,1′-cycloalkyl substituents. Of the compounds described here analogues 2d (CB1,
