Copper (I) chloride catalyzed synthesis of diaryl ethers in ionic liquids under mild conditions

Synthetic Communications

Volumn 33, Issue 20, 2003, Pages 3607-3614

  Chauhan, S M S ^a   Jain, Nidhi ^a   Kumar, Anil ^a   Srinivas, K A ^a  

^a UNIVERSITY OF DELHI   (India)

Author keywords

Copper(I) chloride; Diaryl ethers; Ionic liquid

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE; 1 BUTYL 3 METHYLIMIDAZOLIUM TETRAFLUOROBORATE; 2 NITROPHENYLPHENYL ETHER; 4 CHLOROPHENYLPHENYL ETHER; 4 METHOXYPHENYL 4 NITROPHENYL ETHER; 4 METHOXYPHENYLPHENYL ETHER; 4 NITROPHENYLPHENYL ETHER; COPPER CHLORIDE; DIPHENYL ETHER; ETHER DERIVATIVE; IMIDAZOLE DERIVATIVE; PHENYL 2 TOLYL ETHER; PHENYL 4 TOLYL ETHER; UNCLASSIFIED DRUG;

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

EID: 0141865661     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120024748     Document Type: Article

References (29)

1. Yasuzawa, T.K.; Shirahata, H.; Sano, K-13, a novel inhibitor of angiotensin converting enzyme produced by micromonospora halophytica subsp. exilisiaII. structure determination. J. Antibiot. 1987, 40, 455-458.
2. Boger, D.L.; Patane, M.A.; Zhou, J. Total synthesis of bouvadin, Omethyl bouvardin and O-methyl-N-desmethyl bouvardin. J. Am. Chem. Soc. 1994, 116, 8544-8556.
3. Rama Rao, A.V.; Gurjar, M.K.; Reddy, L.; Rao, A.S. Studies directed towards the synthesis of vancomycin and related cyclic peptides. Chem. Rev. 1995, 95, 2135-2167.
4. NAR bases macrocyclization via biaryl ether formation: application in natural product synthesis. Synlett 1997, 133-146.
5. Lindley, J. Copper assisted nucleophilic substitution of aryl halogen. Tetrahedron 1984, 40, 1433-1456.
6. Marcoux, J.F.; Doye, S.; Buchwald, S.L. A general copper catalyzed synthesis of diaryl ethers. J. Am. Chem. Soc. 1997, 119, 10539-10540.
7. Palomo, C.; Oiarbide, M.; Lopez, R.; Bengoa, E.G. Phophazene Pu-But base for the Ullmann biaryl ether synthesis. Chem. Comm. 1998, 2091-2092.
8. Mann, G.; Hartwig, J.F. Palladium catalyzed formation of diaryl ethers from aryl bromides. Electron poor phsphines enhance reaction yields. Tetrahedron Lett. 1997, 38, 8005-8008.
9. Sheldon, R.A. Catalytic reactions in ionic liquids. Chem. Commun. 2001, 2399-2407.
10. Wasserscheid, P.; Keim, W. Ionic liquids - New "solutions" for transition metal catalysis. Angew. Chem. Int. Ed. 2000, 39, 3772-3789.
11. Adams, C.J.; Earle, M.J.; Roberts, G.; Seddon, K.R. Friedel-Crafts reactions in room temperature ionic liquids. Chem. Comm. 1998, 2097-2098.
12. Suarez, P.A.Z.; Dullius, J.E.L.; Einloft, S.; Desouza, R.F.; Dupont, J. The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes. Polyhedron 1996, 15, 1217-1219.
13. Fischer, T.; Sethi, A.; Welton, T.; Woolf, J. A photochemical generation of nitroso-carbonyl intermediates. Tetrahedron Lett. 1999, 40, 793-796.
14. Kaufmann, D.E.; Nouroozian, M.; Henze, H. Molten salts as an efficient medium for palladium catalysed C-C coupling reactions. Synlett 1996, 1091-1092.
15. Morrison, D.W.; Forbes, D.C.; Davis, J.H. Base promoted reactions in ionic liquid solvents. The knoevenagel and Robinson annulation reactions. Tetrahedron Lett. 2001, 42, 6053-6055.
16. Mathews, C.J.; Smith, P.J.; Welton, T. Palladium catalysed Suzuki cross-coupling reactions in ambient temperature ionic liquids. Chem. Commun. 2000, 1249-1250.
17. Anna, M.M.D.; Gallo, V.; Masprorilli, P.; Nobile, C.F.; Romanazzi, G.; Suranna, G.P. Chem. Metal catalysed Michel additions in ionic liquids. Commun. 2002, 434-435.
18. Srinivas, K.A.; Kumar, Anil; Chauhan, S.M.S. Epoxidation of alkenes with hydrogen peroxide catalysed by iron(III) porphyrins in ionic liquids. Chem. Commun. 2002, 2456-2457.
19. Welton, T. Room temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 1999, 99, 2071-2083.
20. Earle, M.J.; Mc Cormac, P.B.; Seddon, K.R. Regioselective alkylation in ionic liquids. Chem. Commun. 1998, 2245-2246.
21. Weingarten, H. Mechanism of the Ullmann condensation. J. Org. Chem. 1964, 29, 3624-3626.
22. 4,4′-Dinitrobiphenyl was obtained in 15% when potassium phenoxide (1.0 mmol), bromo benzene (0.4 mmol) and CuCl (0.4 mmol) were refluxed in DMF for 15h.
23. Wilkes, J.S.; Zaworotko, M.J. Air and water stable 1-etyl-3-methylimidazolium based ionic liquids. J. Chem. Soc. Chem. Commun. 1992, 965-967.
24. Fuller, J.; Carlin, R.T.; De Lang, H.C.; Haworth, D. Structure of 1-ethyl-3-methylimidazolium hexafluorophosphate, model for room temperature molten salts. J. Chem. Soc. Chem. Commun. 1994, 299-301.
25. Milyakh, S.V.; Ivanova, V.O.; Scheremnykh, N.G. Effect of different factors on the synthesis of diphenyl oxide Nefteperab. Neftekhim. 1973, 6, 25-26.
26. Ullmann, F.; Sponagel, B. The phenylation of phenols. Justus Liebigs Ann. Chem. 1906, 350, 83-107.
27. Mattan, I.A.; Falk, J.C. The synthesis and saponificaiton kinetics of some 4′-substituted 4-phenoxy phenyl acetates. Can. J. Chem. 1968, 46, 1156-1158.
28. Bamkole, T.O.; Hirst, J.; Udoessien, E.I. The ortho: para ratio in aromatic nucleophilic substitution. Part II. J. Chem. Soc. Perkin Trans. 2 1973, 2114-2119.
29. Steller, K.E.; Letsinger, R.L. Effect of distant substituents on photo-induced aromatic substitution reactions. J. Org. Chem. 1970, 35, 308-312.