Comparison of copper(II) acetate promoted N-arylation of 5,5-dimethyl hydantoin and other imides with triarylbismuthanes and aryl boronic acids

Synlett

Volumn , Issue 14, 2006, Pages 2290-2292

  Hügel, Helmut M ^a   Rix, Colin J ^a   Fleck, Karin ^a  

^a RMIT UNIVERSITY   (Australia)

Author keywords

Arylations; Hydantoins; Imides; Organoboron chemistry; Organometallic reagents

Indexed keywords

5,5 DIMETHYLHYDANTOIN; BORONIC ACID DERIVATIVE; COPPER ACETATE; HYDANTOIN DERIVATIVE; IMIDE; PHTHALIMIDE; SUCCINIMIDE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; STRUCTURE ANALYSIS;

EID: 33748703296     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949638     Document Type: Article

References (34)

1. Miyaura, N.; Suzuki, A. J. Chem. Soc., Chem. Commun. 1979, 866.
2. Chan, D. M. T.; Monaco, K. L.; Wang, R. P.; Winters, M. P. Tetrahedron Lett. 1998, 38, 2933.
3. Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
4. Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, M. Tetrahedron Lett. 1998, 39, 2941.
5. Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 43, 5400.
6. (a) Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 4397.
7. (b) Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1361.
8. (a) Beringer, F. M.; Brierley, A.; Drexier, M.; Gindler, E. M.; Lumpkin, C. C. J. Am. Chem. Soc. 1953, 75, 2708.
9. (b) Kang, S.-K.; Lee, S.-H.; Lee, D. Synlett 2000, 1022.
10. Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J. P.; Khaasi, J. Tetrahedron Lett. 1987, 28, 3111.
11. (a) Barton, D. H. R.; Finet, J. P. Pure Appl. Chem. 1987, 59, 937.
12. (b) Barton, D. H. R.; Finet, J. P.; Khamsi, J. Tetrahedron Lett. 1987, 28, 887.
13. Lam, P. Y. S.; Vincent, D.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2002, 43, 3091.
14. (a) Lam, P. Y. S.; Deudon, S.; Hauptman, E.; Clark, C. G. Tetrahedron Lett. 2001, 42, 2427.
15. (b) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Yadhav, P. K. Tetrahedron Lett. 2001, 42, 3415.
16. Brouillette, W. J.; Jestkov, V. P.; Brown, M. L.; Aktar, M. S.; Delory, T. M.; Brown, G. B. J. Med. Chem. 1994, 37, 3289.
17. (a) Stella, V. J. Adv. Drug Deliv. Rev. 1996, 19, 311.
18. (b) Narisawa, S.; Stella, V. J. J. Pharm. Sci. 1998, 87.
19. Moguilewsky, M.; Fiet, J.; Tournernine, C.; Raynaud, J. P. J. Steroid Biochem. 1986, 24, 139.
20. Yee, N. K. Org. Lett. 2000, 2, 2781.
21. Battmann, T.; Bonfils, A.; Branche, C.; Humbert, J.; Goubert, F.; Teutsch, G.; Philibert, D. J. Steroid Biochem. Mol. Biol. 1994, 48, 55.
22. Meusel, M.; Gütschow, M. Org. Prep. Proced. Int. 2004, 36, 391.
23. (a) Muri, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 133.
24. (b) Wolfe, J. P.; Wagan, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
25. (c) Yang, B. Y.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
26. (a) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046.
27. (b) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. I; Negishi, E.-I.; de Meijere, A., Eds.; Wiley: New York, 2002, 1051-1096.
28. (c) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
29. (d) Hartwig, J. F. Synlett 1997, 329.
30. (e) Daramano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
31. Chan, D. M. T. Tetrahedron Lett. 1996, 27, 9013.
32. Lan, J.-b.; Zhang, G.-L.; Yu, X.-Q.; You, J.-S.; Chen, L.; Yan, M.; Xie, R.-G. Synlett 2004, 1095.
33. Chernick, E. T.; Ahrens, M. J.; Scheidt, K. A.; Wasielewski, M. B. J. Org. Chem. 2005, 70, 1486.
34. 2 (3 × 50 mL) and EtOAc (3 × 50 mL). The solvent was removed in vacuo. The residue was mixed with, and impregnated on, silica gel, and then separated via flash column chromatography (hexane-EtOAc; 4:1 for phthalimide derivatives; 2:3 for succinimide and 5,5′-dimethylhydantoin derivatives).