Tert-butoxide-mediated arylation of benzene with aryl halides in the presence of a catalytic 1,10-phenanthroline derivative

Journal of the American Chemical Society

Volumn 132, Issue 44, 2010, Pages 15537-15539

  Shirakawa, Eiji ^a   Itoh, Ken Ichi ^a   Higashino, Tomohiro ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL HALIDES; ARYLATIONS; BENZENE DERIVATIVES; PHENANTHROLINES; TRANSITION METAL CATALYSTS;

BENZENE; CATALYSTS; SODIUM; TRANSITION METALS;

METAL HALIDES;

1,10 PHENANTHROLINE; BENZENE; IODINE DERIVATIVE; SODIUM;

ARTICLE; ARYLATION; CATALYSIS; CATALYST;

EID: 78149233868     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1080822     Document Type: Article

References (33)

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12. The coupling of aryl halides with π-deficient N-heteroarenes but not with benzene derivatives has been reported to be promoted by KO t -Bu under microwave irradiation.
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14. The reaction was conducted in a 35 mL oven-dried pressure-resistant tube (Ace Pressure Tube, Ace Glass 864807, available via Aldrich). Heating the reaction mixture at a temperature (bath temperature = 185 °C) above the boiling point of the solvent (benzene: 80 °C) causes some pressure and, consequently, reduces the temperature in the tube to 155 °C.
15. 1H NMR.
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18. Our reaction system (entry 22 of Table 1) did not promote the coupling of 1a with 2a at 80 °C. ICP-AES and/or -MS analysis showed that the contents of transition metals (Fe, Co, Ni, Cu, Ru, Rh, Pd, Ag, Ir, Pt, Au) in NaO t -Bu and Ph-phen are less than 0.05 ppm except for Fe (1.0 ppm) and Cu (0.18 ppm) in NaO t -Bu.
19. The reaction of 1a with pyrazine (30 equiv) and NaO t -Bu (2 equiv) in the presence (10 mol%) or absence of Ph-phen at 100 °C for 12 h gave 2-(p -tolyl)pyrazine in a yield (conv) of 63% (>99%) or 7% (16%), respectively.
20. For the coupling of benzonitrile, an increased amount of NaO t -Bu was used to compensate loss from its reaction with the nitrile moiety.
21. Similar selectivities were observed also in competition reactions between 2a and 2b as well as 2a and 2c. For details, see Supporting Information.
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28. After the reaction giving 3a under similar conditions of entry 22 of Table 1, 74% of Ph-phen was recovered, implying that it acts as a catalyst rather than an initiator. See Supporting Information for details.
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32. The reaction of 1a (1.0 equiv) with 2b or 2c (120 equiv) under the same conditions as entry 20 of Table 1 (155 °C, 6 h) gave 3m or 3o in 40% or 5% yield (85% or 19% conversion of 1a), respectively.
33. Very recently, a report on KO t -Bu-mediated arylation of benzene with aryl iodides in the presence of a catalytic N,N -dimethylethylenediamine appeared. Liu, W.; Cao, H.; Zhang, H.; Zhang, H.; Chung, K. H.; He, C.; Wang, H.; Kwong, F. Y.; Lei, A. J. Am. Chem. Soc. doi: 10.1021/ja103050x.