N-benzylbenzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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