2-Iodobiphenyl

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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: Toluene (100 mL) was bubbled with nitrogen for 15 min, followed by the addition of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.0 g, 2.4 mmol) and Pd2(dba)3 (0.5 g, 0.6 mmol). The mixture was bubbled with nitrogen for 15 min, then [1,1′-biphenyl]-2-amine (3.4 g, 20.0 mmol), 2-iodobiphenyl (3.5 mL, 20.0 mmol), and sodium tert-butoxide (3.8 g, 40.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 21 h. After cooling, the reaction mixture was filtered through a silica pad and washed with 50% DCM/hexane. The solvent was removed in vacuo. The residue was dissolved in 1,2-dichlorobenzene (80 mL). After that, 4-iodoanisole (18.7 g, 80.0 mmol), potassium carbonate (5.5 g, 40.0 mmol), copper powder (1.3 g, 20.0 mmol), and 18-crown-6 ether (5.3 g, 20.0 mmol) were added. The resultant mixture was bubbled with nitrogen for 30 min. The mixture was refluxed for 88 h. After cooling, the solvent was removed in vacuo and the residue was purified by flash chromatography using 25% DCM/hexane to yield N-([1,1′-biphenyl]-2-yl)-N-(4-methoxyphenyl)-[1,1′-biphenyl]-2-amine (7.4 g, 87% yield) as a colorless oil. Toluene (100 mL) was bubbled with nitrogen for 15 min The mixture was bubbled with nitrogen for 15 min The mixture was bubbled with nitrogen for 15 min refluxed for 21 h After cooling the reaction mixture was filtered through a silica pad washed with 50% DCM/hexane The solvent was removed in vacuo The residue was dissolved in 1,2-dichlorobenzene (80 mL) The resultant mixture was bubbled with nitrogen for 30 min The mixture was refluxed for 88 h After cooling the solvent was removed in vacuo the residue was purified by flash chromatography

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

実験手順: Toluene (100 mL) was bubbled with nitrogen for 15 min, followed by the addition of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.0 g, 2.4 mmol) and Pd2(dba)3 (0.5 g, 0.6 mmol). The mixture was bubbled with nitrogen for 15 min, then [1,1′-biphenyl]-2-amine (3.4 g, 20.0 mmol), 2-iodobiphenyl (3.5 mL, 20.0 mmol), and sodium tert-butoxide (3.8 g, 40.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 21 h. After cooling, the reaction mixture was filtered through a silica pad and washed with 50% DCM/hexane. The solvent was removed in vacuo. The residue was dissolved in 1,2-dichlorobenzene (80 mL). After that, 4-iodoanisole (18.7 g, 80.0 mmol), potassium carbonate (5.5 g, 40.0 mmol), copper powder (1.3 g, 20.0 mmol), and 18-crown-6 ether (5.3 g, 20.0 mmol) were added. The resultant mixture was bubbled with nitrogen for 30 min. The mixture was refluxed for 88 h. After cooling, the solvent was removed in vacuo and the residue was purified by flash chromatography using 25% DCM/hexane to yield N-([1,1′-biphenyl]-2-yl)-N-(4-methoxyphenyl)-[1,1′-biphenyl]-2-amine (7.4 g, 87% yield) as a colorless oil. Toluene (100 mL) was bubbled with nitrogen for 15 min The mixture was bubbled with nitrogen for 15 min The mixture was bubbled with nitrogen for 15 min refluxed for 21 h After cooling the reaction mixture was filtered through a silica pad washed with 50% DCM/hexane The solvent was removed in vacuo The residue was dissolved in 1,2-dichlorobenzene (80 mL) The resultant mixture was bubbled with nitrogen for 30 min The mixture was refluxed for 88 h After cooling the solvent was removed in vacuo the residue was purified by flash chromatography

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A cooled (−78° C.) solution of commercially available 2-iodo-1,1′-biphenyl (680 mg; 2.43 mmol) in anh. THF (20 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.52 ml; 2.43 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of ethyl 4-((tert-butylsulfinyl)imino)-2-methylbutanoate (600 mg; 2.43 mmol) in anh. THF (5 ml) was added to the cooled reaction mixture, and stirring was continued from −78° C. to 0° C. over 1 h. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (80 ml), Et2O (250 ml) and water (75 ml). The separated organic layer was then washed with brine (75 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded ethyl 4-([1,1′-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)-2-methylbutanoate as a mixture of stereoisomers. LC-MS (conditions A): tR=0.93 min.; [M+H]+: 401.79 g/mol and tR=0.94 min.; [M+H]+: 401.80 g/mol. stirring was continued from −78° C. to 0° C. over 1 h The resulting reaction mixture The separated organic layer was then washed with brine (75 ml) dried over anh. MgSO4 filtered concentrated to dryness under reduced pressure Purification by FC (DCM/MeOH=25/1)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A cooled (−78° C.) solution of commercially available 2-iodo-1,1′-biphenyl (680 mg; 2.43 mmol) in anh. THF (20 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.52 ml; 2.43 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of ethyl 4-((tert-butylsulfinyl)imino)-2-methylbutanoate (600 mg; 2.43 mmol) in anh. THF (5 ml) was added to the cooled reaction mixture, and stirring was continued from −78° C. to 0° C. over 1 h. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (80 ml), Et2O (250 ml) and water (75 ml). The separated organic layer was then washed with brine (75 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded ethyl 4-([1,1′-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)-2-methylbutanoate as a mixture of stereoisomers. LC-MS (conditions A): tR=0.93 min.; [M+H]+: 401.79 g/mol and tR=0.94 min.; [M+H]+: 401.80 g/mol. stirring was continued from −78° C. to 0° C. over 1 h The resulting reaction mixture The separated organic layer was then washed with brine (75 ml) dried over anh. MgSO4 filtered concentrated to dryness under reduced pressure Purification by FC (DCM/MeOH=25/1)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A cooled (−78° C.) solution of commercially available 2-iodo-1,1′-biphenyl (1.916 g; 6.84 mmol) in anh. THF (62 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (4.27 ml; 6.84 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 4-((tert-butylsulfinyl)imino)butanoate (1.500 g; 6.84 mmol) in anh. THF (8 ml) was added to the cooled reaction mixture, and stirring was continued from −78° C. to 0° C. over 1 h. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (80 ml), Et2O (250 ml) and water (75 ml). The separated organic layer was then washed with brine (75 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded methyl 4-([1,1′-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)butanoate. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 374.12 g/mol. stirring was continued from −78° C. to 0° C. over 1 h The resulting reaction mixture The separated organic layer was then washed with brine (75 ml) dried over anh. MgSO4 filtered concentrated to dryness under reduced pressure Purification by FC (DCM/MeOH=25/1)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A cooled (−78° C.) solution of commercially available 2-iodo-1,1′-biphenyl (1.916 g; 6.84 mmol) in anh. THF (62 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (4.27 ml; 6.84 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 4-((tert-butylsulfinyl)imino)butanoate (1.500 g; 6.84 mmol) in anh. THF (8 ml) was added to the cooled reaction mixture, and stirring was continued from −78° C. to 0° C. over 1 h. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (80 ml), Et2O (250 ml) and water (75 ml). The separated organic layer was then washed with brine (75 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded methyl 4-([1,1′-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)butanoate. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 374.12 g/mol. stirring was continued from −78° C. to 0° C. over 1 h The resulting reaction mixture The separated organic layer was then washed with brine (75 ml) dried over anh. MgSO4 filtered concentrated to dryness under reduced pressure Purification by FC (DCM/MeOH=25/1)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A cooled (−78° C.) solution of commercially available 2-iodo-1,1′-biphenyl (617 mg; 2.20 mmol) in anh. THF (5 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.50 ml; 2.40 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 5-((tert-butylsulfinyl)imino)pentanoate (514 mg; 2.20 mmol) in anh. THF (2 ml) was added to the cooled reaction mixture, and stirring at −78° C. was continued for 10 min., and then at −20° C. for 2 h. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (15 ml), Et2O (30 ml) and water (15 ml). The separated organic layer was then washed with brine (15 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=7/3) afforded methyl 5-([1,1′-biphenyl]-2-yl)-5-(1,1-dimethylethylsulfinamido)pentanoate as a yellow oil. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 387.83 g/mol. stirring at −78° C. was continued for 10 min. at −20° C. for 2 h The resulting reaction mixture The separated organic layer was then washed with brine (15 ml) dried over anh. MgSO4 filtered concentrated to dryness under reduced pressure Purification by FC (heptane/AcOEt=7/3)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A cooled (−78° C.) solution of commercially available 2-iodo-1,1′-biphenyl (617 mg; 2.20 mmol) in anh. THF (5 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.50 ml; 2.40 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 5-((tert-butylsulfinyl)imino)pentanoate (514 mg; 2.20 mmol) in anh. THF (2 ml) was added to the cooled reaction mixture, and stirring at −78° C. was continued for 10 min., and then at −20° C. for 2 h. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (15 ml), Et2O (30 ml) and water (15 ml). The separated organic layer was then washed with brine (15 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=7/3) afforded methyl 5-([1,1′-biphenyl]-2-yl)-5-(1,1-dimethylethylsulfinamido)pentanoate as a yellow oil. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 387.83 g/mol. stirring at −78° C. was continued for 10 min. at −20° C. for 2 h The resulting reaction mixture The separated organic layer was then washed with brine (15 ml) dried over anh. MgSO4 filtered concentrated to dryness under reduced pressure Purification by FC (heptane/AcOEt=7/3)

反応条件: temp:0.00; pressure:0.00; stir: