Copper-catalyzed N-arylation of sulfonamides with aryl bromides and iodides using microwave heating

Tetrahedron Letters

Volumn 44, Issue 16, 2003, Pages 3385-3386

  He, Huan ^a   Wu, Yong Jin ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE; IODIDE; SULFONAMIDE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; HEATING; MICROWAVE RADIATION;

EID: 0037436943     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00569-0     Document Type: Article

References (11)

1. Hester J.B., Gibson J.K., Cimini M.G., Emmert D.E., Locker P.K., Perricone S.C., Skaletzky L.L., Sykes J.K., West B.E. J. Med. Chem. 34:1991;308-315.
2. Romero D.L., Morge R.A., Genin M.J., Biles C., Busso M., Resnick L., Althaus I.W., Reusser F., Thomas R.C., Tarpley W.G. J. Med. Chem. 36:1993;1505-1508.
3. Serradeil-Le Gal C., Wagnon J., Garcia C., Lacour C., Guiraudou P., Christophe B., Villanova G., Nisato D., Maffrand J.P. J. Clin. Invest. 92:1993;224-231.
4. Turner S.R., Strohbach J.W., Tommasi R.A., Aristoff P.A., Johnson P.D., Skulnick H.I., Dolak L.A., Seest E.P., Tomich P.K., Bohanon M.J., Horng M.M., Lynn J.C., Chong K.-T., Hinshaw R.R., Watenpaugh K.D., Janakiraman M.N., Thaisrivongs S. J. Med. Chem. 41:1998;3467-3476.
5. Yin J., Buchwald S.L. J. Am. Chem. Soc. 124:2002;4043-6048.
6. Yin J., Buchwald S.L. Org. Lett. 2:2000;1101-1104.
7. Lam P.Y.S., Vincent G., Clark C.G., Deudon S., Jadhav P.K. Tetrahedron Lett. 42:2001;3415-3418.
8. The microwave unit used in our experiments is the Smith Creator® from Personal Chemistry. It continuously adjusts the applied wattage to maintain the desired temperature. Reactions were conducted in the Personal Chemistry proprietary 5 mL sealed vials.
9. Perreux L., Loupy A. Tetrahedron. 57:2001;9199-9223.
10. Lange J.H.M., Hofmeyer L.J.F., Hout F.A.S., Osnabrug S.J.M., Verveer P.C., Kruse C.G., Feenstra R.W. Tetrahedron Lett. 43:2002;1101-1104.
11. 3, 100 MHz) δ 121.8, 125.5, 127.2, 129.0, 129.4, 133.0, 136.4, and 139.0. The spectroscopic data is in full agreement with that obtained from an authentic sample purchased from Aldrich.