Synthesis 2020; 52(16): 2357-2363
DOI: 10.1055/s-0039-1691734
paper
© Georg Thieme Verlag Stuttgart · New York

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

Carl Phillip Tüllmann
,
Sebastian Steiner
,
Department of Chemistry, Ludwig-Maximilian-University, Butenandtstraße 5–13, 81377 Munich, Germany   Email: Paul.Knochel@cup.uni-muenchen.de
› Author Affiliations
We thank the Deutsche Forschungsgemeinschaft (DFG) for financial support.
Further Information

Publication History

Received: 24 January 2020

Accepted after revision: 04 February 2020

Publication Date:
20 February 2020 (online)


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·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.

Supporting Information

 
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