Synthesis 2012; 44(22): 3505-3511
DOI: 10.1055/s-0032-1317354
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Imidazole-Derived Ionic Liquids from Monoterpenes by Means of the Sonogashira Reaction

Marcelo G. Speziali*
Instituto de Química, Universidade Federal do Rio Grande do Sul, Av. Bento Gonçalves, 9500, 91501-570, CP 15003, Porto Alegre, RS, Brazil   Fax: +55(51)33087304   Email: marcelo.speziali@ufrgs.br
,
Adriano L. Monteiro
Instituto de Química, Universidade Federal do Rio Grande do Sul, Av. Bento Gonçalves, 9500, 91501-570, CP 15003, Porto Alegre, RS, Brazil   Fax: +55(51)33087304   Email: marcelo.speziali@ufrgs.br
› Author Affiliations
Further Information

Publication History

Received: 10 August 2012

Accepted after revision: 14 September 2012

Publication Date:
17 October 2012 (online)


Abstract

This work reports the functionalization of monoterpenoids with 2-iodo-1-methyl-1H-imidazole using Sonogashira cross-coupling reactions. Natural monoterpenes were also modified to obtain­ the corresponding alkynes which were used in the cross-coupling­ step. After a sequence of cross-coupling–hydrogenation–N-alkylation–ion metathesis, novel ionic liquids were obtained in reasonable yields. The obtained products can be used as scaffolds for the further synthesis of new ionic liquids derived from terpenoids and for new, potentially bioactive materials, e.g. polycyclic monocationic scaffolds. All obtained products show the characteristics of a room temperature ionic liquid (RTIL).

Supporting Information

 
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