Three-component synthesis of amine derivatives using benzylic and allylic alcohols as N-alkylating agents in the absence of external catalysts and additives

摘要

The direct employment of benzylic and allylic alcohols as N-alkylating agents provides a useful synthetic route for amine derivatives by avoiding the preactivation of the hydroxy groups of alcohols. Herein we report a novel by-product-catalyzed three-component synthesis of amine derivatives from readily available benzylic and allylic alcohols, acyl chlorides (chloroformates or sulfonyl chlorides), and hexamethyldisilazane (HMDS). In the absence of external catalysts and additives, a range of benzylic and allylic alcohols have been transformed into the corresponding N-alkyl amides (carbamates or sulfonamides) in good to excellent yields. Furthermore, by-product TMSCl and its decomposition into HCl have been found to be responsible for promoting the three-component reaction of benzylic (or allylic) alcohols with acyl chlorides (chloroformates or sulfonyl chlorides) and HMDS. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).