17296-28-5Relevant academic research and scientific papers
Radical dearomatization of arenes and heteroarenes
Crich, David,Patel, Mitesh
, p. 7824 - 7837 (2007/10/03)
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.
Oxazoles Are Masked Carboxyls That Activate Ortho-Leaving Groups in Nucleophilic Aromatic Substitution
Cram, Donald J.,Bryant, Judi A.,Doxsee, Kenneth M.
, p. 19 - 22 (2007/10/02)
Oxazoles substituted in their 2-positions with 2-methoxy-, 2-fluoro-, or 2,6-difluorophenyl groups, and in their 4,5-positions with methyls or phenyls, were treated with ArMgBr or ArLi to give substituted biphenyl or terphenyl products.The oxazole groups were subsequently converted to esters, acids, or amides.These reactions provide a new unsymmetrical aryl-aryl coupling synthon.
