Ruthenium-catalysed codimerisation of myrcene with methyl acrylate: Catalyst screening and mechanistic discussions

The codimerisation of 1,3-dienes and acrylic compounds is a feasible strategy for the synthesis of functionalised alkenes. In this work, a direct approach to novel C13 esters for the flavour and fragrance industry was performed by codimerisation of myrcene and methyl acrylate. Thus, a further contribution was demonstrated for the use of terpenes as a biobased feedstock for fine chemicals. Different homogeneous ruthenium catalysts showed high activities in the target reaction. Systematic optimisation of the reaction parameters were carried out, resulting in high regioselectivities and yields. A comparison of codimerisation products described in the literature and the observed C13 esters led to mechanistic discussions.

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► An approach to novel C13 esters for the flavour and fragrance industry was performed.
► Homogeneous catalysts containing ruthenium appeared to be very active.
► Systematic optimisations concerning the different reaction parameters were investigated.
► Selection criteria for capable ruthenium complexes could be derived.