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Volumn 2, Issue 5, 2005, Pages 407-409

Arylboronic acid-lead tetraacetate-copper diacetate: A one-pot system for copper-catalyzed N-arylation under neutral conditions

Author keywords

Arylboronic acid; Aryllead triacetate; Copper diacetate catalysis; Diarylamines; Ullman modified N arylation

Indexed keywords


EID: 46149087567     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178054405995     Document Type: Review
Times cited : (4)

References (35)
  • 14
    • 0001751213 scopus 로고    scopus 로고
    • Barton-modified Ullmann condensation reaction: (a) Barton, D. H. R.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1987, 28, 887.
    • Barton-modified Ullmann condensation reaction: (a) Barton, D. H. R.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1987, 28, 887.
  • 17
    • 0000217424 scopus 로고    scopus 로고
    • Barton-Arylplumbane modified Ullmann condensation reaction: (a) Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1987, 28, 3111.
    • Barton-Arylplumbane modified Ullmann condensation reaction: (a) Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1987, 28, 3111.
  • 19
    • 0034115347 scopus 로고    scopus 로고
    • Chan-Lam modified Ullmann condensation reaction: (a) Lam, P. Y. S., Clark, C. G.; Saubern, S.; Adams, J.; Averill, K.; Chan, D. M. T.; Combs, A. P. Synlett 2000 674.
    • Chan-Lam modified Ullmann condensation reaction: (a) Lam, P. Y. S., Clark, C. G.; Saubern, S.; Adams, J.; Averill, K.; Chan, D. M. T.; Combs, A. P. Synlett 2000 674.
  • 23
    • 0037181057 scopus 로고    scopus 로고
    • Cappuccio, k A.; Ayala, I.; Elliott, G. I.; Szundi, I.; Lewis, J.; Konopelski, J. P.; Barry, B. A.; Einarsdottir, O. J. Am. Chem. Soc. 2002, 124, 1750.
    • (b) Cappuccio, k A.; Ayala, I.; Elliott, G. I.; Szundi, I.; Lewis, J.; Konopelski, J. P.; Barry, B. A.; Einarsdottir, O. J. Am. Chem. Soc. 2002, 124, 1750.
  • 27
    • 46149085564 scopus 로고    scopus 로고
    • General procedure for the transmetallation of arylboronic acid derivatives to aryllead triacetates: A mixture of lead tetraacetate (4.9 mmol, mercuric diacetate (0.48 mmol) in chloroform (6 cm3) was stirred at 40 °C for 15 min. The arylboronic acid (4.5 mmol) was then added, and the resulting mixture was stirred at 40 °C for 6 hours. The solvent was concentrated under reduced pressure to a small light petroleum was added and the solution kept overnight at 5 °C. The resulting solid was filtered and dried, 2-Methoxyphenyl)lead triacetate: m.p. 63 °C (from chloroform, 1H NMR (CDCl3, 300 MHz) δ 2.07 (s, 9H, OAc, 3.88 (s, 3H, 2-OMe, 7.03 (dd, 1H, J, 8.2 and 1.3 Hz, 3-H, 7.44 (ddd, 1H, J, 8.2 and 7.3 and 1.5 Hz, 4-H, 7.16 (ddd, 1H, J, 8.0, 7.2 and 1.3 Hz, 5-H, 7.76 dd, 1H, J, 8.0 and 1.5 Hz, 6-H
    • 3, 300 MHz) δ 2.07 (s, 9H, OAc), 3.88 (s, 3H, 2-OMe), 7.03 (dd, 1H, J = 8.2 and 1.3 Hz, 3-H), 7.44 (ddd, 1H, J = 8.2 and 7.3 and 1.5 Hz, 4-H), 7.16 (ddd, 1H, J = 8.0, 7.2 and 1.3 Hz, 5-H), 7.76 (dd, 1H, J = 8.0 and 1.5 Hz, 6-H).
  • 33
    • 46149095906 scopus 로고    scopus 로고
    • General procedure for the arylation of 3,4-dimethylaniline to arylamines: A mixture of lead teffaacetate (4.06 mmol, mercuric diacetate (0.48 mmol) in chloroform (6 cm3) was stirred at 40 °C for 15 min. The arylboronic acid (4.5 mmol) was added, and the resulting mixture was stirred at 40 °C for 6 hours. Then, copper diacetate (0.41 mmol) and the amine (4.12 mmol) were added and the rqsulting mixture was stirred for 5 hours. The mixture was filtered through Celite and the solvent was evaporated. The residue was purified by flash column chromatography on silicagel (pentanes/methylene dichloride 8/2, The resulting diarylamine was finally recrystallized from pentane. 3-Nitrophenyl(3,4-dimethylphenyl) amine: m.p. 97 °C. 1H NMR (CDCl3, 300 MHz) δ 2.27 (s, 3H, 4-Me, 2.28 (s, 3H, 3-Me, 5.45 (br s, 1H, NH, 6.93 (dd, 1H, J, 8.0 and 2.0 Hz, 5-H, 6.95 (d, 1H, J, 2.0 Hz, 2-H, 7.13 (1H, d, J, 7.9 Hz, 6-H, 7.22 dt, 1H, J, 8.1, 2.1 Hz, 6
    • 2: calcd. C, 69,62; H, 5,98; N, 11,31; found: C, 69,41; H, 5,82; N, 11,56%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.