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

Carl Phillip Tüllmann, Sebastian Steiner, Paul Knochel*

*Department of Chemistry, Ludwig-Maximilian-University, Butenandtstraße 5–13, 81377 Munich, Germany, Email: Paul.Knochelcup.uni-muenchen.de

C. P. Tüllmann, S. Steiner, P. Knochel, Synthesis, 2020, 52, 2357-2363.

DOI: 10.1055/s-0039-1691734


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Abstract

N-Protected (1H-tetrazol-5-yl)zinc pivalates are storable solids with appreciably air and moisture stability. They are obtained in high yields by deprotonation using the mixed zinc-magnesium base TMPZnCl·Mg(OPiv)2. Subsequent cross-couplings and copper-catalyzed electrophilic aminations using hydroxylamine benzoates give access to functionalized 1H-tetrazoles.

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Key Words

zinc, tetrazoles, heterobiaryls, Negishi cross-coupling, amination, organozinc pivalates


ID: J66-Y2020