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Volumn 129, Issue 34, 2007, Pages 10354-10355

Selective palladium-catalyzed arylation of ammonia: Synthesis of anilines as well as symmetrical and unsymmetrical di- and triarylamines

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; ANILINE DERIVATIVE; AROMATIC AMINE; HALIDE; LIGAND; PALLADIUM;

EID: 34548249621     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074681a     Document Type: Article
Times cited : (305)

References (41)
  • 1
    • 24144441333 scopus 로고    scopus 로고
    • 2nd ed, de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim, Germany
    • Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004, p 699.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions , pp. 699
    • Jiang, L.1    Buchwald, S.L.2
  • 18
  • 30
    • 33845611136 scopus 로고    scopus 로고
    • 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
    • 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.
  • 39
    • 34548264251 scopus 로고    scopus 로고
    • 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
    • 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.
  • 41
    • 18244428502 scopus 로고    scopus 로고
    • 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.
    • 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.