Zn-Catalyzed Direct Synthesis of 3-Iodo-1,3-dienes from ¿-Allenols

Abstract

In recent years, the chemistry of allenes has attracted the attention of many chemists giving rise to numerous studies due to the presence of a cumulated diene in the structure of the compound. Therefore, these allenes have allowed to prepare a variety of compounds of chemical and biological interest.

On the other hand, 3-iodo-1,3-dienes are interesting species in organic chemistry because of its wide reactivity. They can undergo Diels-Alder cycloaddition, palladium-catalyzed cross-coupling reactions such as Stille, Negishi, Sonogashira and carbonylation, as well as solvolysis and metallation reactions.

We wish to report herein a new protocol that allows to obtain 3-iodo-1,3-dienes through a sustainable process starting from α-allenols. In this new synthetic route, zinc (II) derivatives are used as metallic promoter which are low cost and are also non-polluting species for the environment