Preparation and Reactions of Mono- and Bis-Pivaloyloxyzinc Acetylides

Tuellmann, Carl Phillip; Chen, Yi-Hung; Schuster, Robin J. and Knochel, Paul (2018): Preparation and Reactions of Mono- and Bis-Pivaloyloxyzinc Acetylides. In: Organic Letters, Vol. 20, No. 15: pp. 4601-4605

Abstract

Mono-pivaloyloxyzinc acetylide and bis-pivaloyloxyzinc acetylide were selectively prepared from ethynylmagnesium bromide in quantitative yields. These zinc reagents readily underwent Negishi cross-couplings with (hetero)aryl iodides or bromides as well as subsequent Sonogashira cross-couplings. 1,3-Dipolar cycloadditions of these zinc acetylides with benzylic azides produced zincated and bis-zincated triazoles which were trapped with several electrophiles. An opposite regioselectivity compared to the Cu-catalyzed click-reactions was observed.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1523-7060
• Language: English