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Homologation of Monoterpenoids into New Sesquiterpenoids via Tandem Isomerisation/Claisen Rearrangement Reactions with Three‐Component Ruthenium Catalysts,and Ru(methallyl)2(COD) Revealed by High Throughput Screening Techniques
Authors:Jrme Le&#x;Ntre  Rachid Touzani  Olivier Lavastre  Christian Bruneau  Pierre&#x;H Dixneuf
Abstract:A catalytic system B based on a ruthenium source Ru3(CO)12, a bulky imidazolinium salt and Cs2CO3 appears very efficient for the transformation of a 1,7‐diene into a γ,δ‐unsaturated aldehyde via tandem isomerisation/Claisen reactions. 1,6‐Dienes arising from the terpenoids menthone and myrtenal were selectively transformed into the corresponding unsaturated aldehydes with catalyst B . High throughput experiments were undertaken to evaluate other multicomponent catalysts: metal source/ligand/base for these tandem reactions. An unexpected catalyst was found to be Ru(methallyl)2(COD) which can operate without additional ligand or reagent.
Keywords:alkene isomerisation  Claisen reaction  high throughput screening  ruthenium catalysts  terpenoids  unsaturated aldehydes
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