An efficient copper-catalyzed coupling of aryl halides with imidazoles

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2657-2660

  Kiyomori, Ayumu ^a   Marcoux, Jean François ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; HALIDE; IMIDAZOLE DERIVATIVE; N ARYLIMIDAZOLE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0033515805     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00291-9     Document Type: Article

References (21)

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11. 3 in the presence of a copper salt gives N-p- tolylimidazole in good yield: López-Alvarado, P.; Avendaño, C.; Menéndez, J. C. J. Org. Chem. 1995, 60, 5678-5682.
12. Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10540.
13. 4. Although 1.5 equiv of the imidazole was typically employed, an excess amount of the aryl halide could alternatively be used: 3.0 mmol of iodobenzene was coupled with 2.0 mmol of 4-phenylimidazole to give the desired products in 96% yield based on the imidazole. When the amount of iodobenzene was reduced to 2.0 mmol, an 86% yield was realized under the same conditions.
14. Lindley, J. Tetrahedron 1984, 40, 1433-1456 and references therein.
15. The synthesis and characterization of these 4-substituted imidazoles has been reported: (a) 4-methyl-1 -phenylimidazole: see reference 1j.
16. 1,4-diphenylimidazole: Dodson, R. J. Am Chem. Soc. 1950, 72, 1478; Ali, A.; Saksena, R. K. J. Indian Chem. Soc. 1981, 58, 624-625.
17. 1,4-diphenylimidazole: Dodson, R. J. Am Chem. Soc. 1950, 72, 1478; Ali, A.; Saksena, R. K. J. Indian Chem. Soc. 1981, 58, 624-625.
18. Use of pyridine-type ligands in copper-assisted nucleophilic substitution reactions has been reported. For example, see: Ito, T.; Watanabe, K. Bull. Chem. Soc. Jpn. 1968, 41, 419-423; Kondratov, S. A.; Shein, S. M. Zh. Org. Khim. 1979, 15, 2387-2390.
19. Use of pyridine-type ligands in copper-assisted nucleophilic substitution reactions has been reported. For example, see: Ito, T.; Watanabe, K. Bull. Chem. Soc. Jpn. 1968, 41, 419-423; Kondratov, S. A.; Shein, S. M. Zh. Org. Khim. 1979, 15, 2387-2390.
20. Bacon, R. G. R.; Hill, H. A. O. J. Chem. Soc. 1964, 1097.
21. It is noteworthy that dba is completely consumed in the course of the reactions, although no products derived from dba could be detected by GC analysis of the reaction mixture. This resulted in products which were yellow- or orange-colored after chromatographic purification, although they were found to be pure by NMR, GC, and conbustion analysis. Decolorization of these was possible either by recrystallization or by distillation.