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Barton-modified Ullmann condensation reaction: (a) Barton, D. H. R.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1987, 28, 887.
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Barton-Arylplumbane modified Ullmann condensation reaction: (a) Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1987, 28, 3111.
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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.
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46149085564
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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
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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).
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28
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33645418976
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Criegee, R.; Dimroth, P.; Schempf, R. Chem. Ber. 1957, 90, 1337.
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0001187901
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0021672373
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Combes, S.1
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Siri, D.3
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46149095906
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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
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2: calcd. C, 69,62; H, 5,98; N, 11,31; found: C, 69,41; H, 5,82; N, 11,56%.
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