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A novel method for the desulfonation of secondary amines is described. Alkali metals absorbed into nanostructured silica (M-SG) were found to be useful solid-state reagents for the desulfonation of a range of N,N-disubstituted sulfonamides. M-SG reagents are room-temperature-stable free-flowing powders that retain the chemical reactivity of the parent metal, decreasing the danger and associated cost of using reactive metals.

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Amines Q 0120Alkali Metals in Silica Gel (M-SG): A New Reagent for Desulfonation of Amines.-Various secondary and primary amines are deprotected with Na 2 K-silica gel reagent followed by quenching with water. Detosylation of the aziridine derivative (IX) requires the milder Na-silica gel reagent to prevent ring-opening. The reaction is also applicable to tosylated aza-kryptands. Solid acidic salts as NH4Cl, HCO2NH4 orNH4)2HPO4, included in situ as a proton source instead of water, provide similar results. -(NANDI, P.; REDKO, M. Y.; PETERSEN, K.; DYE, J. L.; LEFENFELD, M.; VOGT, P. F.; JACKSON*, J. E.; Org. Lett. 10 (2008) 23, 5441-5444; Dep. Chem., Mich. State Univ., East Lansing, MI 48824, USA; Eng.) -R. Steudel 17-075