Copper-Catalyzed Electrophilic Amination of Diorganozinc Reagents

Journal of the American Chemical Society

Volumn 126, Issue 18, 2004, Pages 5680-5681

  Berman, Ashley M ^a   Johnson, Jeffrey S ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; DIORGANOZINC; HYDROXYLAMINE; O ACYL HYDROXYLAMINE; ORGANIC COMPOUND; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; GRIGNARD REACTION; REACTION TIME; STOICHIOMETRY;

EID: 2442544350     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049474e     Document Type: Article

References (21)

1. Lev, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
2. Hartwig, J. F. In Handbook of Organopalladian Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley: New York, 2002; Vol. 1. pp 1051-1096.
3. Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
4. Dembech, P.; Seconi, G.; Ricci, A. Chem. Eur. J. 2000, 6, 1281-1286.
5. Greck, C.; Genêt, J. P. Synlett 1997, 741-748.
6. Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947-1980.
7. Smulik, J. A.; Vedejs, E. Org. Lett. 2003, 5, 4187-4190.
8. Greck, C.; Bischoff, L.; Ferreira, F.; Genêt, J. P. J. Org. Chem. 1995, 60, 7010-7012.
9. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641-643.
10. Beak, P.; Basu, K. C.; Li, J. J. J. Org. Chem. 1999, 64, 5218-5223.
11. Boche, G.; Mayer, N.; Bernheim, M.; Wagner, K. Angew. Chem., Int. Ed. 1978, 17, 687-688.
12. (a) Erdik, E.; Ay, M. Synth. React. Inorg. Met.-Org. Chem. 1989, 19, 663-668.
13. (b) Erdik, E.; Daskapan, T. J. Chem. Soc., Perkin Trans. I 1999, 3139-3142.
14. (c) Erdik, E.; Daskapan, T. Synth. Commun. 1999, 29, 3989-3997.
15. (a) Tsutsui, H.; Hayashi, Y.; Narasaka, K. Chem. Lett. 1997, 317-318.
16. (b) Tsutsui, H.; Ichikawa, T.; Narasaka, K. Bull. Chem. Soc. Jpn. 1999, 72, 1869-1878.
17. For a tabular summary of conditions that were evaluated, see the Supporting Information.
18. Amination of RZnX with dialkyl azodicarboxylates: Velarde-Ortiz, R.; Guijarro, A.; Rieke, R. D. Tetrahedron Lett. 1998, 39, 9157-9160.
19. Oguri. T.; Shioiri, T.; Yamada, S. Chem. Pharm. Bull. 1975, 23, 167-172.
20. An analogous reaction of PhMgBr and O-benzoyl-N-hydroxypiperidine gives N-phenylpiperidine in 4% isolated yield in the absence of CuOTf and 13% yield with 2.5 mol % CuOTf.
21. Biloski, A. J.; Ganem, B. Synthesis 1983. 537-538.