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Synthesis 2018; 50(05): 1007-1014
DOI: 10.1055/s-0036-1591879
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© Georg Thieme Verlag Stuttgart · New York

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

Marco Seifried
a   Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria   Email: danny.mueller@tuwien.ac.at
,
Christian Knoll
a   Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria   Email: danny.mueller@tuwien.ac.at
,
Jan M. Welch
b   Atominstitut, TU Wien, Stadionallee 2, 1020 Vienna, Austria
,
Danny Müller*
a   Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria   Email: danny.mueller@tuwien.ac.at
,
Peter Weinberger
a   Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria   Email: danny.mueller@tuwien.ac.at
› Author Affiliations
Further Information

Publication History

Received: 30 October 2017

Accepted after revision: 01 December 2017

Publication Date:
11 January 2018 (online)

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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

Supporting Information

    Supporting information for this article is available online at https:<//doi.org/10.1055/s-0036-1591879.
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