Alkali metals in silica gel as mild and efficient detosylation reagents for secondary amines

ORGN 636

Partha Nandi, nandipar@msu.edu1, James E Jackson, jackson@chemistry.msu.edu1, Mikhail Y. Redko, redko@msu.edu2, James L Dye, dye@msu.edu1, and Michael Lefenfeld, michael@signachem.com3. (1) Department of Chemistry, Michigan State University, East lansing, MI 48823, (2) Department of Chemistry, Michigan State University, East Lansing, MI 48824-1322, (3) SiGNa Chemistry, 530 East 76th Street, Suite 9E, New York, NY 10021
Treatment of a range of para toluene-sulfonamides of secondary amines with our recently reported alkali metal-silica gel (M-SG) materials effected clean desulfonation at room temperature in THF. The easy-to-handle stage I forms of Na2K, K2Na, Na and K in large-pore silica gel were used together with the solid state proton sources NH4Cl, (NH4)2HPO4, KHP (potassium hydrogen phthalate), NaHCO3, or NaH2PO4. Reaction yields varied between 70-85%.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006