Silyl triflate-accelerated additions of catalytically generated zinc acetylides to N-phenyl nitrones

Terminal alkynes readily form zinc acetylides in the presence of iPr(2)NEt and 20 mol % ZnBr2, then attack N-phenyl nitrones activated by trimethylsilyl trifluoromethanesulfonate. Deprotection with aqueous acid yields N-hydroxyl propargylamine. Yields are generally high for nitrones derived from aromatic aldehydes. Control experiments suggest that silyl triflate has a significant accelerating effect upon the reaction. (C) 2014 Elsevier Ltd. All rights reserved.