Some unexpected products from attempted halogen exchange in 2-nitrohaloaromatic systems

Catalytic Halogen‐Exchange Fluorination of 4‐Chlorobenzaldehyde to 4‐Fluorobenzaldehyde, a Greener Process

“…Defluorination of product under the drastic reaction conditions is usually observed in halogen‐exchange fluorination [18] . Because the boiling points of the fluorination product and the defluorination product are very close, the purity of the product will be affected when defluorination is significant.…”

“…The side product control related to the defluorination of the product was also studied as it is commonly observed under drastic reaction conditions. [9,18]…”

“…We paid attention not only to factors that may affect the reaction itself but also to those aspects of product isolation as well as materials recycling. The side product control related to the defluorination of the product was also studied as it is commonly observed under drastic reaction conditions [9,18] …”

Tetramethylammonium Fluoride Tetrahydrate-Mediated Transition Metal-Free Coupling of Aryl Iodides with Unactivated Arenes in Air

“…We first studied the coupling of the substrate 2-nitroiodobenzene, 1a, with benzene as solvent (Table 1). When the coupling reaction was conducted in Ar atmosphere in the presence of TMAF, which was used as a fluoride source in our previous work, 62) biaryl product 2a was obtained in low yield (entry 1). The use of TMAF•4H 2 O, which is air stable, gave the same yield (entry 2).…”

“…[56][57][58][59][60][61] Very recently, we reported the amide base-mediated biaryl coupling of aryl iodides and arenes. 62) Tetramethylammonium fluoride (TMAF) and hexamethyldisilazane (HMDS) were used to generate the amide base in situ. During the investigation, it was found that the coupling of 2-nitroiodobenzene with benzene was driven by TMAF in the absence of HMDS.…”