* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Patent: US6337404, 2002, B1, . Location in patent: Example 2
[2] Patent: US6342637, 2002, B1, . Location in patent: Example 2
[3] Russian Chemical Bulletin, 2003, vol. 52, # 3, p. 607 - 615
[4] Anales de la Real Sociedad Espanola de Fisica y Quimica, vol. 20, p. 476[5] Chem. Zentralbl., 1923, vol. 94, # III, p. 1157
[6] Justus Liebigs Annalen der Chemie, 1874, vol. 174, p. 212[7] Chemische Berichte, 1874, vol. 7, p. 53
[8] Australian Journal of Chemistry, 1977, vol. 30, p. 103 - 111
2
[ 92-93-3 ]
[ 6242-98-4 ]
[ 80334-07-2 ]
Reference：
[1] Journal of the American Chemical Society, 1938, vol. 60, p. 424,426
[2] An. Farm. Bioquim. Buenos Aires, 1933, vol. 4, p. 60,86[3] An. Farm. Bioquim. Buenos Aires, 1934, vol. 5, p. 28
[4] Journal of the American Chemical Society, 1938, vol. 60, p. 424,426
[5] An. Farm. Bioquim. Buenos Aires, 1933, vol. 4, p. 60,86[6] An. Farm. Bioquim. Buenos Aires, 1934, vol. 5, p. 28
[7] Inorganica Chimica Acta, 2014, vol. 423, # 1, p. 238 - 241
[8] Inorganica Chimica Acta, 2014, vol. 423, # PA, p. 238 - 241
3
[ 92-93-3 ]
[ 6242-98-4 ]
Reference：
[1] Russian Chemical Bulletin, 2003, vol. 52, # 3, p. 607 - 615
[2] Journal of the Chemical Society, 1926, p. 2046[3] Journal of the Chemical Society, 1928, p. 245,246
[4] Anales de la Asociacion Quimica Argentina (1921-2001), 1932, vol. 20, p. 8,34, 45
[5] Journal of the American Chemical Society, 1938, vol. 60, p. 424,426
[6] Journal of the Chemical Society, 1931, p. 1359,1362
[7] An. Farm. Bioquim. Buenos Aires, 1933, vol. 4, p. 60,86[8] An. Farm. Bioquim. Buenos Aires, 1934, vol. 5, p. 28
[9] Journal of Organometallic Chemistry, 1997, vol. 549, # 1-2, p. 127 - 137
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[ 106-37-6 ]
[ 6242-98-4 ]
Reference：
[1] European Journal of Organic Chemistry, 2014, vol. 2014, # 14, p. 2942 - 2955
5
[ 106-37-6 ]
[ 24067-17-2 ]
[ 6242-98-4 ]
[ 3282-11-9 ]
Reference：
[1] Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3730 - 3733
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[ 673-40-5 ]
[ 98-95-3 ]
[ 6242-98-4 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1972, p. 2555 - 2562
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[ 92-52-4 ]
[ 6242-98-4 ]
Reference：
[1] Justus Liebigs Annalen der Chemie, 1874, vol. 174, p. 212[2] Chemische Berichte, 1874, vol. 7, p. 53
[3] Justus Liebigs Annalen der Chemie, 1874, vol. 174, p. 212[4] Chemische Berichte, 1874, vol. 7, p. 53
8
[ 65-85-0 ]
[ 6242-98-4 ]
Reference：
[1] Justus Liebigs Annalen der Chemie, 1874, vol. 174, p. 212[2] Chemische Berichte, 1874, vol. 7, p. 53
[3] Justus Liebigs Annalen der Chemie, 1874, vol. 174, p. 212[4] Chemische Berichte, 1874, vol. 7, p. 53
9
[ 92-93-3 ]
[ 7732-18-5 ]
[ 7726-95-6 ]
[ 7705-08-0 ]
[ 64-19-7 ]
[ 6242-98-4 ]
[ 80334-07-2 ]
Reference：
[1] Journal of the American Chemical Society, 1938, vol. 60, p. 424,426
[2] An. Assoc. quim. arg., 1932, vol. 20, p. 8,21
[3] An. Farm. Bioquim. Buenos Aires, 1933, vol. 4, p. 60,86[4] An. Farm. Bioquim. Buenos Aires, 1934, vol. 5, p. 28
10
[ 1211-40-1 ]
[ 6242-98-4 ]
Reference：
[1] Justus Liebigs Annalen der Chemie, 1874, vol. 174, p. 212[2] Chemische Berichte, 1874, vol. 7, p. 53
11
[ 92-93-3 ]
[ 7726-95-6 ]
[ 7705-08-0 ]
[ 64-19-7 ]
[ 6242-98-4 ]
[ 80334-07-2 ]
Reference：
[1] Journal of the American Chemical Society, 1938, vol. 60, p. 424,426
[2] An. Assoc. quim. arg., 1932, vol. 20, p. 8,21
[3] An. Farm. Bioquim. Buenos Aires, 1933, vol. 4, p. 60,86[4] An. Farm. Bioquim. Buenos Aires, 1934, vol. 5, p. 28
With N-Bromosuccinimide; [bis(acetoxy)iodo]benzene; [NiBr(C5H3N(C3H2N2Me)2)]Br; trifluoroacetic acid; at 25℃; for 24h;Sealed tube; Inert atmosphere;
General procedure: To 2 mL CF3COOH (or D2O), 0.25 mmol substrate, 0.5 mmol oxidizing agent, 0.375 mmol NBS and 5 mol% catalyst were added. The reagents were taken in a specially designed tube (10 mL), were purged with N2 gas, and sealed; the mixture was stirred for 24 h at room temperature. Next, the volatiles were removed under reduced pressure. The brominated products were analyzed by 1HNMR spectroscopy and the yields were calculated by GC/MS using dodecane as an internal standard.
With N-Bromosuccinimide; [(nickel(II))(bromide)(NC5H3(N2C3H2(Me))2)](bromide); [bis(acetoxy)iodo]benzene; trifluoroacetic acid; at 25℃; for 24h;Inert atmosphere; Sealed tube;
General procedure: To 2 mL CF3COOH (or D2O), 0.25 mmol substrate, 0.5 mmol oxidizing agent, 0.375 mmol N BS and 5 mol% catalyst were added.The reagents were taken in a specially designed tube (10 mL), were purged with N2 gas, and sealed; the mixture was stirred for 24 h at room temperature. Next, the volatiles were removed under reduced pressure. The brominated products were analyzed by 1HNMR spectroscopy and the yields were calculated by GC/MS using dodecane as an internal standard.
The process according to the invention is suitable for example for preparing: ... 4'-phenyl-2-nitrobiphenyl 4'-trifluoromethyl-2-nitrobiphenyl 4'-fluoro-4-nitrobiphenyl 4'-chloro-4-nitrobiphenyl 4'-bromo-4-nitrobiphenyl 4'-methyl-4-nitrobiphenyl 4'-cyano-4-nitrobiphenyl 2-nitrobiphenyl ...
General procedure: In a oven-dried flask and under nitrogen flow, benzenediazonium o-benzenedisulfonimide (1a, 161mg, 0.5mmol) was added to a suspension of 4-methoxyphenylboronic acid (3a, 91mg, 0.6mmol), [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) (2:1) toluene adduct (39mg, 0.025mmol, 5mol%), Cs2CO3 (325mg, 1mmol) in THF (5mL). The resulting mixture was stirred at room temperature for 2h; the completion of the reaction was confirmed by the absence of azo coupling with 2-naphthol. Then, the reaction mixture was poured into diethyl ether/water (100mL, 1:1). The aqueous layer was separated and extracted with diethyl ether (50mL). The combined organic extracts were washed with water (50mL), dried with Na2SO4 and evaporated under reduced pressure. GC-MS analyses of the crude residue showed 4-methoxybiphenyl (4a), MS (EI): m/z 184 (M+) as the major product, besides traces of biphenyl, MS (EI): m/z 154 (M+), 4,4'-dimethoxybiphenyl, MS (EI): m/z 214 (M+), N-phenyl-o-benzenedisulfonimide, MS (EI): m/z 295 (M+). The crude residue was purified on a short column, eluting with petroleum ether/diethyl ether (9:1). The only isolated product was the title compound (4a, 81mg, 88% yield).
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