N-benzylidenebenzenesulfonamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of allyl magnesium bromide (12 mmol) in Et2O (1.0 M, 12 mL) was added dropwise over 10 min to a stirred solution of N-benzylidenebenzene sulfonamide (2.5 g, 10.2 mmol) in THF (40 mL) under N2. After 2 h the mixture was poured into brine and extracted with EtOAc. These extracts were washed with H2O and brine then dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica eluting with CH2Cl2 to give the benzenesulfonamide as a white solid (1.9 g, 65%). 1H NMR (360 MHz, CDCl3) δ 2.44–2.48 (2H, m), 4.39–4.45 (11H, m), 4.79 (11H, d, J=5.6 Hz), 5.04–5.10 (2H, m), 5.46–5.58 (1H, m), 7.04–7.07 (2H, m), 7.15–7.19 (3H, m), 7.32–7.37 (2H, m), 7.43–7.48 (1H, m), 7.64–7.67 (2H, m). extracted with EtOAc These extracts were washed with H2O and brine then dried (MgSO4) concentrated under reduced pressure The residue was purified by column chromatography on silica eluting with CH2Cl2

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 5 mL flask opened to the air, to a clear solution of N-benzylidenebenzene sulfonamide (100 mg, 0.408 mmol) in benzene (0.4 mL) was added dimethylphenylsilane (125 μL, 0.816 mmol). The flask was placed in a 60° C. bath and iodo[bis(triphenylphosphine)] oxorhenium(V) (18 mg, 0.021 mmol) was added. The resulting brown solution was heated at 60° C. for 2 hours. To the reaction mixture was added methanol (0.4 mL) followed by trifluoroacetic acid (35 μL), and heating continued for an additional 2 h. The crude reaction mixture was directly applied to a SiO2 column and chromatographed eluting with 1:1 hexanes:diethyl ether to afford N-phenylsulfonylbenzylamine (87 mg, 86% yield) as a slightly yellow solid. was placed in a 60° C. heating The crude reaction mixture chromatographed eluting with 1:1 hexanes

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 5 mL flask opened to the air, to a clear solution of N-benzylidenebenzene sulfonamide (100 mg, 0.408 mmol) in benzene (0.4 mL) was added dimethylphenylsilane (125 μL, 0.816 mmol). The flask was placed in a 60° C. bath and iodo[bis(triphenylphosphine)] oxorhenium(V) (18 mg, 0.021 mmol) was added. The resulting brown solution was heated at 60° C. for 2 hours. To the reaction mixture was added methanol (0.4 mL) followed by trifluoroacetic acid (35 μL), and heating continued for an additional 2 h. The crude reaction mixture was directly applied to a SiO2 column and chromatographed eluting with 1:1 hexanes:diethyl ether to afford N-phenylsulfonylbenzylamine (87 mg, 86% yield) as a slightly yellow solid. was placed in a 60° C. heating The crude reaction mixture chromatographed eluting with 1:1 hexanes

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of allyl magnesium bromide (12 mmol) in Et2O (1.0 M, 12 mL) was added dropwise over 10 min to a stirred solution of N-benzylidenebenzene sulfonamide (2.5 g, 10.2 mmol) in THF (40 mL) under N2. After 2 h the mixture was poured into brine and extracted with EtOAc. These extracts were washed with H2O and brine then dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica eluting with CH2Cl2 to give the benzenesulfonamide as a white solid (1.9 g, 65%). 1H NMR (360 MHz, CDCl3) δ 2.44–2.48 (2H, m), 4.39–4.45 (11H, m), 4.79 (11H, d, J=5.6 Hz), 5.04–5.10 (2H, m), 5.46–5.58 (1H, m), 7.04–7.07 (2H, m), 7.15–7.19 (3H, m), 7.32–7.37 (2H, m), 7.43–7.48 (1H, m), 7.64–7.67 (2H, m). extracted with EtOAc These extracts were washed with H2O and brine then dried (MgSO4) concentrated under reduced pressure The residue was purified by column chromatography on silica eluting with CH2Cl2

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 5 mL flask opened to the air, to a clear solution of N-benzylidenebenzene sulfonamide (100 mg, 0.408 mmol) in benzene (0.4 mL) was added dimethylphenylsilane (125 μL, 0.816 mmol). The flask was placed in a 60° C. bath and iodo[bis(triphenylphosphine)] oxorhenium(V) (18 mg, 0.021 mmol) was added. The resulting brown solution was heated at 60° C. for 2 hours. To the reaction mixture was added methanol (0.4 mL) followed by trifluoroacetic acid (35 μL), and heating continued for an additional 2 h. The crude reaction mixture was directly applied to a SiO2 column and chromatographed eluting with 1:1 hexanes:diethyl ether to afford N-phenylsulfonylbenzylamine (87 mg, 86% yield) as a slightly yellow solid. was placed in a 60° C. heating The crude reaction mixture chromatographed eluting with 1:1 hexanes