2-(Phenylseleno)ethanesulfon-amide as a novel protecting group for aniline that can be deprotected by a radical reaction

Construction of 5H‐Dibenzo[c,e]azepine Framework from Dibenzothiophene Dioxides andN‐Benzylimines through SNAr Reactions

“…1,3‐Diphenylpropene was prepared according to the literature procedure with some modification [30] . A 300‐mL two‐neck flask was charged with Pd(OAc) 2 (449 mg, 2.00 mmol), tri( o ‐tolyl)phosphane (2.43 g, 8.00 mmol), iodobenzene (5.71 g, 28.0 mmol), allylbenzene (2.36 g, 20.0 mmol), and triethylamine (50 mL).…”

“…Preparation of 1,3-Diphenylpropene 1,3-Diphenylpropene was prepared according to the literature procedure with some modification. [30] A 300-mL two-neck flask was charged with Pd(OAc) 2 (449 mg, 2.00 mmol), tri(o-tolyl)phosphane (2.43 g, 8.00 mmol), iodobenzene (5.71 g, 28.0 mmol), allylbenzene (2.36 g, 20.0 mmol), and triethylamine (50 mL). The resulting mixture was refluxed for 10 h. After evaporation to remove triethylamine, the residue was dissolved in ethyl acetate (50 mL), quenched with sat.…”

Enantioselective Selenol-ene Using Rh-Hydride Catalysis

“…Compared to thiols, selenols have a lower p K a (the p K a s of benzeneselenol and thiophenol are 5.9 and 6.6, respectively) and weaker X–H bonds (67–74 and 78 kcal/mol, respectively) . Selenols are known to readily add into Michael acceptors, including α,β-unsaturated ketones, a vinylsulfonamide, nitroalkenes, and N -vinyl lactams . There has also been difunctionalization of alkenes to form selenides emerging; however, enantioselective variants of this approach remain unknown .…”

Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes

“…In 1988, Hevesi reported the first hydroselenation of conjugated enones in the presence of ZnCl 2 , 8 although the desired adduct was controlled by the substrates used. Then the hydroselenation of α,β-unsaturated ketones was found to be catalyzed by ceric ammonium nitrate (CAN) 9 or β-cyclodextrin, 10 while the nitroalkenes 11 and vinylsulfonamide 12 were self-promoted in the absence of any catalyst (Scheme 1A). The substrates, such as those involving weakly activated or nonelectronically activated CC bonds, were rarely reported.…”