Preparation and Reactions of (1H-Tetrazol-5-yl)zinc Pivalates

Tuellmann, Carl Phillip; Steiner, Sebastian und Knochel, Paul (2020): Preparation and Reactions of (1H-Tetrazol-5-yl)zinc Pivalates. In: Synthesis-Stuttgart, Bd. 52, Nr. 16: S. 2357-2363

Abstract

The preparation and reactivity of new solid heterocyclic organozinc reagents, namely N-protected (1H-tetrazol-5-yl)zinc pivalates, as storable solids with appreciably air and moisture stability are reported. They are obtained in high yields from protected 1H-tetrazoles by deprotonation using the mixed zinc-magnesium base TMPZnCl center dot Mg(OPiv)(2) (abbreviated as TMPZnOPiv;TMP = 2,2,6,6-tetramethylpiperidyl). Subsequent cross-couplings and copper-catalyzed electrophilic aminations using hydroxylamine benzoates give access to functionalized 1H-tetrazoles while tolerating many functional groups.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0039-7881
• Sprache: Englisch