Expeditious functionalization of quinolines in positions 2 and 8 via polyfunctional aryl- and heteroarylmagnesium intermediates

Synthesis

Volumn , Issue 2, 2003, Pages 233-242

  Staubitz, Anne ^a   Dohle, Wolfgang ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cross coupling; Functionalized heterocycles; Functionalized organomagnesium reagents; Iodine magnesium exchange; Palladium catalysis

Indexed keywords

AROMATIC HYDROCARBONS; NITROGEN COMPOUNDS;

CROSS-COUPLING REACTIONS;

SYNTHESIS (CHEMICAL);

8 IODO 2 TRIFLUOROMETHANESULFONYLOXYQUINOLINE DERIVATIVE; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; IODINE; MAGNESIUM DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; QUINOLINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; NEGISHI CROSS COUPLING REACTION; SYNTHESIS;

EID: 0037281225     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-36828     Document Type: Article

References (15)

1. Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 5th ed.; Blackwell Science: Oxford, 1998.
2. (a) Rottländer, M.; Boymond, L.; Bérillon. L.; Leprâtre, A.; Varchi, G.; Avolio, S.; Laaziri, H.; Quéguiner, G.; Ricci, A.; Cahiez, G.; Knochel, P. Chem.-Eur. J. 2000, 6, 767.
3. (b) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565.
4. Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618.
5. (a) Lindsay, D. M.; Dohle, W.; Jensen, A. E.; Kopp, F.; Knochel, P. Org. Lett. 2002, 4, 1819.
6. (b) Sy, W.-W. Synth. Commun. 1992, 22, 3215.
7. (c) Toste, D.; McNulty, J.; Still, I. W. J. Synth. Commun. 1994, 24, 1617.
8. (d) McNulty, J.; Still, I. W. J. Tetrahedron Lett. 1991, 32, 4875.
9. Varchi, G.; Jensen, A. E.; Dohle, W.; Ricci, A.; Cahiez, G.; Knochel, P. Synlett 2001, 477.
10. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
11. Piers, E.; Wong, T.; Coish, P. D.; Rogers, C. Can. J. Chem. 1994, 72, 1816.
12. Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
13. Knochel, P.; Millot, N.; Rodriguez, A. L.; Tucker, C. A. Org. React. 2001, 58, 417.
14. Negishi, E. Acc. Chem. Res. 1982, 15, 340.
15. Brown, D. J.; Waring, P. Aust. J. Chem. 1973, 26, 443.