Highly efficient heterogenous catalyst for O-arylation of phenols with aryl halides using natural ferrous chamosite

Applied Clay Science

Volumn 51, Issue 1-2, 2011, Pages 131-137

  Arundhathi, R ^a   Sreedhar, B ^a   Parthasarathy, G ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Aryl halides; C O bond formation; Chamosite; Ethers; Natural clay; Reusability

Indexed keywords

ARYL BROMIDES; ARYL HALIDES; ARYL IODIDES; ARYLATIONS; C-O BOND FORMATION; CATALYZED COUPLING; CHAMOSITE; DIARYL ETHERS; HETEROGENOUS CATALYSTS; HIGH YIELD; LIGAND-FREE; NATURAL CATALYSTS; NATURAL CLAYS; NUMBER OF CYCLES;

BROMINE COMPOUNDS; CATALYSIS; CATALYSTS; ETHERS; METAL HALIDES; ORGANIC COMPOUNDS; REACTION KINETICS; REUSABILITY;

PHENOLS;

CATALYST; ETHER; FILTRATION; HALIDE; PHENOL;

EID: 78650738467     PISSN: 01691317     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.clay.2010.11.014     Document Type: Article

References (18)

1. Bistri O., Correa A., Bolm C. Iron-catalyzed C-O cross-couplings of phenols with aryl iodides. Angewandte Chemie International Edition 2008, 47:586-588.
2. Blankenstein J., Zhu J. Conformation-directed macrocyclization reactions. European Journal of Organic Chemistry 1998, 2005:1949-1964.
3. Burgos C.H., Barder T.E., Huang X., Buchwald S.L. Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: understanding ligand effects. Angewandte Chemie International Edition 2006, 45:4321-4326.
4. Chan D.M.T., Monaco K.L., Wang R.P., Winters M.P. New N- and O-arylations with phenylboronic acids and cupric acetate. Tetrahedron Letters 2008, 39:2933-2936.
5. Deng H., Jung J.K., Liu T., Kuntz K.W., Snapper M.L., Hoveyda A.H. Total synthesis of anti-HIV agent chloropeptin I. Journal of American Chemical Society 2003, 125:9032-9034.
6. Evans D.A., Katz J.L., West T.R. Synthesis of L, L-isodityrosine. Tetrahedron Letters 1998, 30:2053-2056.
7. Evans D.A., Dinsmore C.J., Watson P.S., Ward M.R., Richardson T.I., Trotter B.W., Katz J.L. Nonconventional stereochemical issues in the design of the synthesis of the vancomycin antibiotics: challenges imposed by axial and nonplanar chiral elements in the heptapeptide aglycons. Angewandte Chemie International Edition 1998, 37:2704-2708.
8. Frlan R., Kikelj D. Recent progress in diaryl ether synthesis. Synthesis 2006, 2271-2285.
9. Ley S.V., Thomas A.W. Modern synthetic methods for copper-mediated C(aryl)- O, C(aryl)-N, and C(aryl)-S bond formation., 2003. Angewandte Chemie International Edition 2003, 42:5400-5449.
10. Mann G., Hartwig J.F. Palladium-catalyzed formation of diaryl ethers from aryl bromides. Electron poor phosphines enhance reaction yields. Tetrahedron Letters 1997, 46:8005-8008.
11. Nicolaou K.C., Natarajan S., Li H., Jain N.F., Hughes R., Solomon M.E., Ramanjulu J.M., Boddy C.N.C., Takayanagi M. Total synthesis of vancomycin aglycon - Part 1: Synthesis of amino acids 4-7 and construction of the AB-COD ring skeleton. Angewandte Chemie International Edition 1998, 37:2708-2714.
12. Nicolaou K.C., Christopher N.C.B., Stefan B., Nicolas W. Chemistry, biology, and medicine of the glycopeptide antibiotics. Angewandte Chemie International Edition 1999, 38:2096-2275.
13. Sawyer J.S. Recent advances in diaryl ether synthesis. Tetrahedron 2000, 56:5045-5065.
14. Sreedhar B., Arundhathi R., Amarnath Reddy M., Parthasarathy G. Highly efficient heterogeneous catalyst for acylation of alcohols and amines using natural ferrous chamosite. Applied Clay Science 2009, 43:425-434.
15. Ullmann F. Ueber eine neue Bildungsweise von Diphenylaminderivaten. Chemische Berichte 1903, 36:2382-2384.
16. Ullmann F. Ueber eine neue Darstellungsweise von Phenyläthersalicylsäur. Chemische Berichte 1904, 37:853-854.
17. Ullmann F., Bielecki Jean Ueber Synthesen in der Biphenylreihe. Chemische Berichte 1901, 34:2174-2185.
18. Ullmann F., Sponagel P. Ueber die Phenylirung von Phenolen. Chemische Berichte 1905, 38:2211-2212.