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Synthesis 2020; 52(16): 2357-2363
DOI: 10.1055/s-0039-1691734
DOI: 10.1055/s-0039-1691734
paper
Preparation and Reactions of (1H-Tetrazol-5-yl)zinc Pivalates
We thank the Deutsche Forschungsgemeinschaft (DFG) for financial support.Weitere Informationen
Publikationsverlauf
Received: 24. Januar 2020
Accepted after revision: 04. Februar 2020
Publikationsdatum:
20. Februar 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
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691734.
- Supporting Information
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