The copper-mediated cross-coupling of phenylboronic acids and N-hydroxyphthalimide at room temperature: Synthesis of aryloxyamines

Organic Letters

Volumn 3, Issue 1, 2001, Pages 139-141

  Petrassi, H Michael ^a   Sharpless, K Barry ^a   Kelly, Jeffery W ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BORONIC ACID DERIVATIVE; COPPER; DRUG; HYDRAZINE DERIVATIVE; N HYDROXYPHTHALIMIDE; N-HYDROXYPHTHALIMIDE; PHTHALIMIDE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; DRUG DESIGN; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINES; BORONIC ACIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; CYCLIZATION; DRUG DESIGN; HYDRAZINES; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; PHTHALIMIDES; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035843284     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0003533     Document Type: Article

References (23)

1. MDL Drug Data Report, MDL Information Systems, Inc., San Leandro, CA.
2. Abele, E.; Lukevies, E. Org. Prep. Proced. Int. 2000, 32, 235.
3. (a) Maly. J. M.; Choong, I. C.: Ellman, J. A. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 2419.
4. (b) Nazarpack-Kandlousy, N., Chernushevich, I. V.; Meng, L.; Yang, Y.; Eliseev, A. V. J. Am. Chem. Soc. 2000, 122, 3358.
5. Choong, I. C.; Ellman, J. A. J. Org. Chem. 1999, 64, 6528.
6. Foot, O. F.; Knight, D. W. Chem. Comm. 2000, 975. For a synthesis of this oxaziridine, see: Vidal, J.; Hannachi, J.-C.; Hourdin, G.; Mulatier, J.-C.; Collet, A. Tetrahedron Lett. 1998, 39, 8845.
7. Foot, O. F.; Knight, D. W. Chem. Comm. 2000, 975. For a synthesis of this oxaziridine, see: Vidal, J.; Hannachi, J.-C.; Hourdin, G.; Mulatier, J.-C.; Collet, A. Tetrahedron Lett. 1998, 39, 8845.
8. Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Org. Prep. Proced. Int. 1977, 29, 594.
9. (a) Cadogan, J. I. G.; Rowley, A. G. Synth. Coinm. 1977, 7, 365.
10. (b) Baldoli, C.; Del Bettero, P.; Licandro, E.; Maiorana, S. Synthesis 1988, 344.
11. (a) Castellino, A. J.; Rapoport, H. J. Org. Chem. 1984, 49, 1348.
12. (b) Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. Synthesis 1977, 1.
13. Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
14. (a) Combs, A. P.; Saubern, S.; Rafalski, M.; Lam, P. Y. S. Tetrahedron Lett. 1999, 40, 1623.
15. (b) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979.
16. (c) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941.
17. (d) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Averill, K. M.; Chan, D. M. T.; Combs, A. Synlett 2000, 5, 674.
18. Herradura, P. S.; Pendola, K. A.; Guy, R. K. Organic Lett. 2000, 2, 2019.
19. (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933.
20. (b) Collman, J. P.; Zhong, M. Organic Lett. 2000, 2, 1233.
21. Several other N-hydroxylamine sources were also evaluated. N-Hydroxynaphthalimide and endo-N-hydroxy-5-norbornene-2,3-dicarboximide were viable N-hydroxylamine sources but afforded inferior yields relative to 1. Cross-couplings with N-hydroxy succinimide and N-hydroxy carbamate were unsuccessful.
22. 2, 25% EtOAc in hexanes) afforded 3a as a white solid (216 mg, 90%). See Supporting Information for characterization of 3a. Notes: Reactions that did not work (e.g., Table 3, entry 16) did not exhibit the brown to green color change. The use of a discolored amine resulted in drastically reduced yields, and therefore all amines were freshly distilled. The use of 4 Å molecular sieves that were not freshly activated gave inferior yields.
23. 2O (2 x 10 mL) to afford the pure HCl salt of 4 (306 mg, 77%). See Supporting Information for characterization of 4.