Preparation and Reactions of Mono- and Bis-Pivaloyloxyzinc Acetylides

Tuellmann, Carl Phillip; Chen, Yi-Hung; Schuster, Robin J. und Knochel, Paul (2018): Preparation and Reactions of Mono- and Bis-Pivaloyloxyzinc Acetylides. In: Organic Letters, Bd. 20, Nr. 15: S. 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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1523-7060
• Sprache: Englisch