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For synthesis of di- and triarylamines from aryl halides and urea in a process that may involve the in situ generation of ammonia: (a) Artamkina, G. A, Sergeev, A. G, Shtern, M. M, Beletskaya, I. P. Russian J. Org. Chem. 2006, 42, 1683
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For synthesis of di- and triarylamines from aryl halides and urea in a process that may involve the in situ generation of ammonia: (a) Artamkina, G. A.; Sergeev, A. G.; Shtern, M. M.; Beletskaya, I. P. Russian J. Org. Chem. 2006, 42, 1683.
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General procedure for the synthesis of unsymmetrical triarylamines: Pd2dba3 (4.6 mg, 0.005 mmol, ligand 4 (8.5 mg, 0.025 mmol, sodium tert-butoxide (202 mg, 2.1 mmol, and aryl halide a (0.5 mmol, if solid) were weighed into an oven-dried test-tube which was sealed with a Teflon screw cap. The tube was then evacuated and back-filled with argon. 1,4-Dioxane (5 mL, ammonia (3 mL of a 0.5 M solution in 1,4-dioxane, 1.5 mmol, and the aryl halide a (0.5 mmol, if liquid) were then added by syringe. The tube was then placed in a preheated oil bath at 80°C for 3 h. At the end of this time the tube was removed from the bath and allowed to cool, and the tube was evacuated and ultrasonicated until the total solvent was reduced to approximately 3 mL and back-filled with argon. The Teflon screw cap was then briefly removed, and ligand 5 (11.9 mg, 0.025 mmol) and aryl halide b (0.45 mmol, if solid) were added. If liqui
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3 (4.6 mg, 0.005 mmol), ligand 4 (8.5 mg, 0.025 mmol), sodium tert-butoxide (202 mg, 2.1 mmol), and aryl halide a (0.5 mmol) (if solid) were weighed into an oven-dried test-tube which was sealed with a Teflon screw cap. The tube was then evacuated and back-filled with argon. 1,4-Dioxane (5 mL), ammonia (3 mL of a 0.5 M solution in 1,4-dioxane, 1.5 mmol), and the aryl halide a (0.5 mmol) (if liquid) were then added by syringe. The tube was then placed in a preheated oil bath at 80°C for 3 h. At the end of this time the tube was removed from the bath and allowed to cool, and the tube was evacuated and ultrasonicated until the total solvent volume was reduced to approximately 3 mL and back-filled with argon. The Teflon screw cap was then briefly removed, and ligand 5 (11.9 mg, 0.025 mmol) and aryl halide b (0.45 mmol) (if solid) were added. If liquid aryl halide b (0.45 mmol) was then added by syringe. The tube was then evacuated, back-filled with argon, and replaced in the oil bath at 80°C for 3 h. At the end of this time the tube was removed from the bath and allowed to cool. If aryl halide c were solid the Teflon screw cap was removed and aryl halide c (0.45 mmol) was added. The tube was then evacuated and back-filled with argon. If aryl halide c was a liquid, the Teflon screw cap was not removed and the aryl halide c (0.45 mmol) was added by syringe. The tube was then placed in a preheated oil bath at 100°C for 16 h. At the end of this time the tube was removed from the bath, the contents diluted with EtOAc, and the mixture filtered through a plug of silica. The solution was then concentrated under reduced pressure, and the residue was purified on the Biotage SP4.
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18244428502
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TPD = N,N′-bis(3-methylphenyl)-N,N′- diphenylbenzidine, for example: Shen, Y.; Klein, M. W.; Jacobs, D. B.; Scott, J. C.; Malliaras, G. G. Phys. Rev. Lett. 2001, 86, 3867.
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TPD = N,N′-bis(3-methylphenyl)-N,N′- diphenylbenzidine, for example: Shen, Y.; Klein, M. W.; Jacobs, D. B.; Scott, J. C.; Malliaras, G. G. Phys. Rev. Lett. 2001, 86, 3867.
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