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Zn-Catalyzed Direct Synthesis of 3-Iodo-1,3-dienes from α-Allenols
* 1 , 2 , 2 , 3
1  Grupo de Sistemas Insaturados y Heterociclos Bioactivos, Unidad Asociada al CSIC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040-Madrid, Spain. Instituto de Química Orgánica General, IQOG-CSIC, J
2  Grupo de Lactamas y Heterociclos Bioactivos, Unidad Asociada al CSIC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040-Madrid, Spain.
3  Instituto de Química Orgánica General, IQOG-CSIC, Juan de la Cierva 3, 28006-Madrid, Spain

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.

Keywords: Allenes; 3-iodo-1,3-dienes; zinc
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