4.8 Article

Catalytic Ester Metathesis Reaction and Its Application to Transfer Hydrogenation of Esters

Journal

ACS CATALYSIS
Volume 6, Issue 6, Pages 3998-4002

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b00827

Keywords

metathesis; esters; pincer complex; transfer hydrogenation; homogeneous catalysis; ruthenium

Funding

  1. Okinawa Institute of Science and Technology

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We report a Ru-complex-catalyzed ester metathesis reaction where an unsymmetrical ester such as ethyl hexanoate can be transformed to a mixture of starting material, hexyl ethanoate, ethyl acetate, and hexyl hexanoate in equal proportions, as expected from a classical metathesis reaction with 0.2 mol % catalyst. A 20x excess of low boiling alcohol, such as ethanol, allows for the transfer of an acyl moiety to the sacrificial low boiling ethyl acetate product, while significantly increasing the functional group tolerance and substrate scope; yields of alcohols can reach 90%, which represents an attractive alternative to current high H-2 pressure hydrogenation protocols for Ru-based ester reduction chemistry. Both reactions have not been reported previously in the field of Ru-catalyzed transformations of the ester functionality.

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