106047-16-9Relevant academic research and scientific papers
Radical dearomatization of arenes and heteroarenes
Crich, David,Patel, Mitesh
, p. 7824 - 7837 (2006)
The stannane-mediated benzeneselenol-catalyzed addition of aryl iodides to a range of arenes and aromatic hetereocycles has been studied. With furan, thiophene, and several carbocyclic arenes, the addition takes place with quenching of the adduct radical by the catalytic selenol leading to moderate yields of aryl-dihydroarenes. With nitrogen heterocycles, on the other hand, it was not possible to suppress aromatization of the adduct radical and fully aromatized products were isolated. Aryl iodides bearing hydrogen bond donating groups in the ortho-position add to nitrogen heterocycles with high selectivity ortho- to the nitrogen, affording a simple one-step synthesis of potential chelating ligands. While 2-iodophenol is an excellent aryl radical source in these reactions, the homologous 1-iodo-2-naphthol fails owing to its reaction with diphenyl diselenide, which gives 1-phenylseleno-2-naphthol in high yield.
THE PYRIDYL CATION AS A REACTIVE INTERMEDIATE IN THE PHOTOREACTION OF IODOPYRIDINES WITH BENZENES
Ohkura, Kazue,Seki, Koh-ichi,Terashima, Masanao,Kanaoka, Yuichi
, p. 3433 - 3436 (1989)
The electrophilic behavior of the reactive entity in the photosubstitution of benzenes with 2-iodopyridine was found to be ascribable to the intermediary 2-pyridyl cation, rather than the electrophilic 2-pyridyl radical.
Direct synthesis of heterobiaryls by radical addition to pyridine: Expeditious synthesis of chelating ligands
Crich, David,Patel, Mitesh
, p. 499 - 504 (2007/10/03)
The addition of aryl radicals to pyridine may be affected in moderate yield on exposure of aryl iodides to tributyltin hydride, AIBN, and diphenyl diselenide in hot pyridine. Mixtures of ortho-, meta-, and para-aryl substituted pyridines are typically obtained. When the iodide is ortho-substituted with a hydrogen bond donor, such as o-iodophenol, significantly improved selectivity for ortho-substituted pyridines, with potential as bidentate chelating ligands, is obtained.
Regioselective Addition ofd Copper-Zinc Aryl Organometallic Reagents to 3-substituted Pyridinium Salts
Shiao, Min-Jen,Chia, Win-Long,Shing, Tai-Li,Chow, Tahsin J.
, p. 2101 - 2121 (2007/10/02)
A number of 3-substituted pyridinium salts are subjected to nucleophilic addition by copper-zinc aryl organometallic reagents.The adducts are oxidized subsequently to form the corresponding 4-arylpyridines.In all the cases 1,4-addition products are obtained predominantly.The regioselectivity can be rationalized according to the hard-soft acid-base principle.Calculations on both charge distributions and FMO coefficients indicate that these reactions may be classified on the basis of the type of soft acid-soft base reactions.The observed γ-attack complies very well with the orientation of the FMO coefficients as estimated by a semiempirical method.
