Solid supported aryl/heteroaryl C-N cross-coupling reactions

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1623-1626

  Combs, Andrew P ^a   Saubern, Simon ^a,b   Rafalski, Maria ^a   Lam, Patrick Y S ^a  

^a DUPONT COMPANY   (United States)

^b CSIRO   (Australia)

Author keywords

Arylation; Coupling reactions; Microwave heating; Polymer support

Indexed keywords

BORONIC ACID DERIVATIVE; CARBON; COPPER ACETATE; HETEROCYCLIC COMPOUND; HYDROGEN; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYMER; PYRIDINE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; MICROWAVE RADIATION; REACTION TIME; SOLID;

EID: 0033605298     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00026-X     Document Type: Article

References (12)

1. 2. A search of the CMC database of biologically active compounds revealed N-arylated heterocycles possessing analgesic, antiinflammatory, antimicrobial, antiasmatic, antibacterial and antirheumatic properties, among others.
2. 3. Lam, P.Y.S.; Clark, C.G.; Saubern, S.; Adams, J.; Winters, M.P.; Chan, D.M.T. and Combs, A., Tettrahedron Lett., 1998, 39, 2941-2944.
3. 4. Although we have only presented examples in this paper employing PS-PEG resin, the reaction works equally well on polystyrene resin.
4. 5. Reactions run under argon and/or without molecular sieves gave low yields of desired N-arylated products.
5. 6. Evans, D.A.; Katz, J.L. and West, T.R., Tetrahedron Lett., 1998, 39, 2937-2940.
6. 7. Solvents with high dielectric constants provide efficient absorption of microwave energy. Strauss, C.R.; Trainor, R.W., Aust. J. Chem., 1995, 48, 1665-1692; Caddick, S., Tetrahedron, 1995, 51, 10403-10432.
7. 7. Solvents with high dielectric constants provide efficient absorption of microwave energy. Strauss, C.R.; Trainor, R.W., Aust. J. Chem., 1995, 48, 1665-1692; Caddick, S., Tetrahedron, 1995, 51, 10403-10432.
8. 8. Larhed, M; Lindeberg, G.; Hallberg A., Tetrahedron Lett., 1996, 37, 8219-8222.
9. 9. Chan, D.M.T.; Monaco, K.L.; Wang, R.-P. and Winters, M.P., Tettrahedron Lett., 1998, 39, 2933-2936.
10. 10. We have been unable to arylate a variety of amides under these conditions.
11. 11. Unpublished results in this laboratory.
12. 12. Suitably adapted 96 well microtiter plates have been utilized for microwave irradiation of reactions in our labs. This technology provides an efficient means of library production, though we have measured with a a thermocouple probe considerable temperature gradients (10-20 degree C) between the outer and inner wells of microtiter plates upon microwave irradiation, leading to non-uniform heating of reactions in this format.