Microwave-assisted copper promoted N-arylation of amines with aryl boronic acids/salts on a KF-alumina surface

Synthetic Communications

Volumn 34, Issue 12, 2004, Pages 2177-2184

  Das, Pralay ^a   Basu, Basudeb ^a  

^a UNIVERSITY OF NORTH BENGAL   (India)

Author keywords

Arylboronic acids; Cupric acetate; KF alumina; Microwaves; N Arylation; Tetraphenylborate salt

Indexed keywords

ALUMINUM OXIDE; AMINE; BORONIC ACID DERIVATIVE; COPPER; COPPER ACETATE; TETRAPHENYLBORON;

ARTICLE; ARYLATION; CHEMICAL BOND; CHEMICAL STRUCTURE; MICROWAVE RADIATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 3142666019     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120038497     Document Type: Article

References (33)

1. (a) Negwer, M. Organic-Chemicals Drugs and Their Synonyms: An International Survey, 7th Ed.; Akademic: Berlin, 1994;
2. (b) Hong, Y.P.; Tanoury, G.J.; Wilkinson, H.S.; Bakale, R.P.; Wald, S.A.; Senanayake, C.H. Palladium catalyzed amination of 2-chloro-1,3-azole derivatives: mild entry to potent H1-antihistaminic norastemizole. Tetrahedron Lett. 1997, 38, 5607.
3. (a) MacDiarmid, A.G.; Epstein, A.J. Science and Applications of Conducting Polymers; Salaneck, W.R., Clark, D.T., Samuelsen, E.J., Eds.; Hilger: New York, 1991;
4. (b) Thayumanavan, S.; Barlow, S.; Marder, S.R. Synthesis of unsymmetrical triarylamines for photonic applications via one-pot palladium-catalyzed aminations. Chem. Mater. 1997, 9, 3231.
5. (a) Ullman, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382;
6. (b) Lindley, J. Copper assisted nucleophilic substitution of aryl halogen. Tetrahedron 1984, 40, 1433;
7. (c) Gauthier, S.; Frechet, J.M.J. Phase-transfer catalysis in the Ullmann synthesis of substituted triphenylamines. Synthesis 1987, 383;
8. (d) Paine, A.J. Mechanisms and models for copper mediated nucleophilic aromatic substitution. 2. Single catalytic species from three different oxidation states of copper in an Ullmann synthesis of triarylamines. J. Am. Chem. Soc. 1987, 109, 1496;
9. (e) Goodbrand, H.B.; Hu, N.-X. Ligand-accelerated catalysis of the Ullmann condensation: application to hole conducting triarylamines. J. Org. Chem. 1999, 64, 670;
10. (f) Arterburn, J.B.; Pannala, M.; Gonzalez, A.M. Catalytic amination of 5-iodouracil derivatives. Tetrahedron Lett. 2001, 42, 1475;
11. (g) Kwong, F.Y.; Klapars, A.; Buchwald, S.L. Copper-catalyzed coupling of alkylamines and aryl iodides: an efficient system even in an air atmosphere. Org. Lett. 2002, 4, 581.
12. (a) Wolfe, J.P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S.L. Rational development of practical catalysts for aromatic carbon-nitrogen bond formation. Acc. Chem. Res. 1998, 31, 805;
13. (b) Yang, B.H.; Buchwald, S.L. Palladium-catalyzed amination of aryl halides and sulfonates. J. Organomet. Chem. 1999, 576, 125;
14. (c) Hartwig, J.F. Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides. Acc. Chem. Res. 1998, 31, 853;
15. (d) Hartwig, J.F. Synthesis, structure, and reactivity of a palladium hydrazonato complex: a new type of reductive elimination reaction to form C-N bonds and catalytic arylation of benzophenone hydrazone. Angew. Chem. Int. Ed. Engl. 1998, 37, 2046;
16. (e) Muci, A.R.; Buchwald, S.L. Practical palladium catalysts for C-N and C-O bond formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, 133.
17. (a) Prashad, M.; Hu, B.; Lu, Y.; Draper, R.; Har, D.; Repic, O.; Blacklock, T.J. β-Hydrogen-containing sodium alkoxides as suitable bases in palladium-catalyzed aminations of aryl halides. J. Org. Chem. 2000, 65, 2612;
18. (b) Link, J.T.; Sorensen, B.; Liu, G.; Pei, Z.; Reilly, E.B.; Leitza, S.; Okasinski, G. Discovery and SAR of diarylsulfide cyclopropylamide LFA-1/ICAM-1 interaction antagonists. Bioorg. Med. Chem. Lett. 2001, 11, 973.
19. (a) Kiyomori, A.; Marcoux, J.-F.; Buchwald, S.L. An efficient copper-catalyzed coupling of aryl halides with imidazoles. Tetrahedron Lett. 1999, 40, 2657;
20. (b) Kelkar, A.A.; Patil, N.M.; Chaudhari, R.V. Copper-catalyzed amination of aryl halides: single-step synthesis of triarylamines. Tetrahedron Lett. 2002, 43, 7143.
21. Chan, D.M.T.; Monaco Wang, R.-P.; Winters, M.P. New N- and O-arylations with phenylboronic acids and cupric acetate. Tetrahedron Lett. 1998, 39, 2933.
22. (a) Lam, P.Y.S.; Clark, C.G.; Saubern, S.; Adams, J.; Winters, M.P.; Chan, D.M.T.; Combs, A. New aryl/heteroaryl C-N bond cross-coupling reactions via arylboronic acid/cupric acetate arylation. Tetrahedron Lett. 1998, 39, 2941;
23. (b) Combs, A.; Saubern, S.; Rafalski, M.; Lam, P.Y.S. Solid supported aryl/heteroaryl C-N cross-coupling reactions. Tetrahedron Lett. 1999, 40, 1623;
24. (c) Lam, P.Y.S.; Clark, C.G.; Saubern, S.; Adams, J.; Averill, K.; Chan, D.M.T.; Combs, A. Copper promoted aryl/saturated heterocyclic C-N bond cross-coupling with arylboronic acid and arylstannane. Synlett. 2000, 674;
25. (d) Evans, D.A.; Katz, J.L.; West, T.R. Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine. Tetrahedron Lett. 1998, 39, 2937;
26. 2-catalyzed coupling of arylboronic acids with imidazoles in water. J. Org. Chem. 2001, 66, 1528.
27. (a) Basu, B.; Jha, S.; Mridha, N.K.; Bhuiyan, M.M.H. Palladium-catalysed amination of halopyridines on a KF-alumina surface. Tetrahedron Lett. 2002, 43, 7967;
28. (b) Basu, B.; Das, P.; Bhuiyan, M.M.H.; Jha, S. Microwave-assisted Suzuki coupling on a KF-alumina surface: synthesis of polyaryls. Tetrahedron Lett. 2003, 44, 3817.
29. (a) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. New solvent-free organic synthesis using focused microwaves. Synthesis 1998, 1213;
30. (b) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Microwave activation in phase transfer catalysis. Tetrahedron 1999, 55, 10851;
31. (c) de la Hoz, A.; Daiz-Ortis, A.; Moreno, A.; Langa, F. Cycloadditions under microwave irradiation conditions: methods and applications. Eur. J. Org. Chem. 2000, 3659;
32. (d) Perreux, L.; Loupy, A. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 2001, 57, 9199;
33. (e) Verma, R.S. Advances in Green Chemistry: Chemical Syntheses Using Microwave Irradiation; Astra Zeneca Research Foundation: Bangalore, 2002.