Unsaturated Aryl and Heteroaryl N1-Tetrazoles from 1-Allyl-1H-tetrazole

Marco Seifried; Christian Knoll; Jan M. Welch; Danny Müller; Peter Weinberger

doi:10.1055/s-0036-1591879

Synthesis, Table of Contents

Synthesis 2018; 50(05): 1007-1014
DOI: 10.1055/s-0036-1591879

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Unsaturated Aryl and Heteroaryl N1-Tetrazoles from 1-Allyl-1H-tetrazole

Marco Seifried

^aInstitute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria Email: danny.mueller@tuwien.ac.at

,

Christian Knoll

^aInstitute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria Email: danny.mueller@tuwien.ac.at

,

Jan M. Welch

^bAtominstitut, TU Wien, Stadionallee 2, 1020 Vienna, Austria

,

Danny Müller*

^aInstitute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria Email: danny.mueller@tuwien.ac.at

,

Peter Weinberger

^aInstitute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria Email: danny.mueller@tuwien.ac.at

› Author Affiliations

Abstract

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Abstract

Unsaturated aryl- and heteroaryl N1-substituted tetrazoles have been exceedingly difficult to access but are nonetheless highly attractive for the preparation of novel multifunctional spin crossover materials. The development of a Heck cross-coupling protocol, featuring good substrate tolerance for aromatic and heteroaromatic substrates overcoming this synthetic challenge is presented. The combination of aqueous THF, triethylamine, and PdCl₂/P(o-tolyl)₃ gave fast reaction rates and good yields. Competition experiments with styrene evidenced a slight preference for reaction with 1-allyl-1H-tetrazole.

Key words

heterocycles - N1-substituted tetrazoles - Heck reaction - cross-coupling - C–C bond formation - aqueous conditions - spin crossover

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References

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