N-alkyl-2-pyridylmethanimines as tuneable alternatives to bipyridine ligands in copper mediated atom transfer radical cyclisation

Tetrahedron Letters

Volumn 40, Issue 19, 1999, Pages 3807-3810

  Clark, Andrew J ^a   Duncalf, David J ^a   Filik, Robert P ^a   Haddleton, David M ^a   Thomas, Gerard H ^b   Wongtap, Hathaichanuk ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b ABBOTT LABORATORIES   (United States)

Author keywords

Addition; Copper; Lactam; Radicals

Indexed keywords

ACETAMIDE DERIVATIVE; BIPYRIDINE DERIVATIVE; COPPER COMPLEX; LIGAND; PYRIDYLMETHANIMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; COMPLEX FORMATION; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS; TEMPERATURE;

EID: 0033532109     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00533-X     Document Type: Article

References (19)

1. 1 Iqbal, J.; Bhatia, B.; Nayyar, N.K. Chem Rev., 1994, 94, 519-564
2. 2 a) Pirrung, F.O.H.; Hiemstra, H.; and Speckamp, W.N. Tetrahedron, 1994, 50, 12415;
3. b) Rachita, M.A.; Slough, G.A. Tet. Lett., 1993, 43, 6821.
4. c) Slough, G.A. Tet. Lett., 1993, 43, 6825
5. 3 Lee, G.M.; Parvez, M.; and Weinreb, S.M. Tetrahedron, 1988, 44, 4671
6. 4 a) Udding, J.H.; Tuijp, K.C.J.M.; Vanzanden, M.N.A.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem., 1994, 59, 1993.
7. b) Udding, J.H Tuijp, K.C.J.M.; Vanzanden, M.N.A.; Hiemstra, H.; Speckamp, W.N. Tetrahedron, 1994, 50, 1907.
8. c) Baldovini, N.; Bertrand, M.-P.; Carrière, A.; Nougier, R.; and Plancher, J-M. J. Org. Chem, 1996, 61, 3205.
9. 5 a) Foroti, L.; Ghelfi, F.; and Pagnoni, U.M. Tetrahedron Lett., 1996, 37, 2077.
10. b) Forti, L.; Ghelfi,F.; Libertini, F.E.; Pagnoni, U.M.; Soragni, E. Tetrahedron, 1997, 53, 17761.
11. 6 De Campo, F.; Lastécouères, D.; Verlhac, J-B.; J. Chem. Soc., Chem. Commun., 1999, 2117.
12. 7 Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; and Itoh, K. J. Org. Chem., 1993, 58, 464
13. 8 Iwamatsu S-I.; Kondo, H.; F. Matsubara, K.; Nagashima, H. Tetrahedron, 1999, 55, 1687.
14. 9 a) Haddleton, D.M.; Duncalf, D.J.; Clark, A.J.; Crossman, M. C.; Kukulj, D. New J. Chem., 1998, 315.
15. b) ) Haddleton, D.M.; Duncalf, D.J.; Kukulj, D.; Crossman, M. C.; Jackson, S.G.; Bon, S.A.F.; Clark, A.J.; Shooter, A.J. Eur. J. Inorg. Chem. 1998, 1799-1806.
16. c) Clark, A.J.; Crossman, M.C.; Duncalf, D.J.; Haddleton, D.M.; Morsley, S.R., Shooter, A.J. J. Chem. Soc., Chem Commun., 1997, 1734.
17. d) Haddleton, D.M.; Clark, A.J.; Duncalf, D.J.; Heming, A.M.; Kukulj, D.; Shooter, A.J. J. Chem. Soc., Dalton Trans, 1998, 381.
18. e) Haddleton, D.M.; Duncalf, D.J.; Kukulj, D.; Shooter, A.J. Clark, A.J. , J. Materials Chemistry, 1998,(8)7, 1525.
19. 10 Haddleton, D.M.; Kukulj, D.; Radigue, A.P.; J. Chem. Soc., Chem. Commun., 1999, 99.