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

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

• References

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