Catalysis Science & Technology
Communication
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Scheme 5 One-pot ruthenium-catalysed oxidative homo-coupling of
1 followed by in situ hydrogenation towards the synthesis of adipic
acid ester derivative 3.
hydrogenation was observed using the silver and copper salts
either solely or combined with each other. However, a
filtration between the two steps was required to remove the
inorganic salts that appear to poison the active ruthenium
catalyst in the hydrogenation step. Overall, the presented
strategy emphasizes the uniqueness of ruthenium catalysts to
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perform
tandem
reactions
involving
C–H
bond
functionalizations and hydrogenations which might be
considered as sustainable to some extent.19
In summary, we have shown that the oxidative homo-
coupling between vinyl derivatives is feasible under
ruthenium catalysis giving valuable 1,3-butadiene products
that are straightforwardly engaged in hydrogenation
sequences to form adipic acid ester derivatives. From a
mechanistic point of view this contribution demonstrates
that ruthenium catalysis enables both oxidative coupling and
isomerization of the Z,E derivative towards the more
thermodynamically favoured E,E isomer. Developments
aiming at ligand design for ruthenium complexes should
enlarge the substrate scope of this methodology.
This work was financially supported by CNRS, Université
de Rennes 1 (Défis scientifiques 2020), ANR-JCJC (ANR-19-
CE07-0039), Fondation Rennes 1 (MSc grant to RK), Region
Bretagne (ARED 2020 No 1715 – PAUSE College de France,
PhD grant to NA).
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rhodium (19450 USD/OZ), iridium (5850 USD/OZ) and
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Conflicts of interest
There are no conflicts to declare.
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