Terminal alkynes readily form zinc acetylides in the presence of iPr2NEt and 20 mol% ZnBr2, then attack N-phenyl nitrones activated by trimethylsilyl trifluoromethanesulfonate. Deprotection with aqueous acid yields the N-hydroxyl propargylamine. Yields are generally high for nitrones derived from aromatic aldehydes. Control experiments suggest that the silyl triflate has a significant accelerating effect upon the reaction.
Copyright © 2014, Elsevier. The definitive version is available at: http://www.journals.elsevier.com/tetrahedron-letters.
Downey, C. Wade, Erin N. Maxwell, and Danielle N. Confair. "Silyl Triflate-accelerated Additions of Catalytically Generated Zinc Acetylides to N-phenyl Nitrones." Tetrahedron Letters 55, no. 35 (August 27, 2014): 4959-961. doi:doi:10.1016/j.tetlet.2014.07.015.
Downey, C. Wade; Maxwell, Erin N.; and Confair, Danielle N., "Silyl triflate-accelerated additions of catalytically generated zinc acetylides to N-phenyl nitrones" (2014). Chemistry Faculty Publications. 15.