Aluminum Triflate—Catalyzed Adamantylation of N-Nucleophiles

Abstract

An efficient method is proposed for N-adamantylation of primary carboxamides and sulfonamides, ethyl carbamate, and 4-nitroaniline using the stoichiometric amount of 1-adamantanol in the presence of 5 mol% aluminum triflate in nitromethane. Similarities and differences between adamantylation of some azoles catalyzed by aluminum triflate in nitromethane and the reaction catalyzed by Brønsted acids were revealed.

Keywords

• adamantylation
• 1-adamantanol
• Lewis acid
• aluminum triflate