Murai Reaction on Furfural Derivatives Enabled by Removable N,N'-Bidentate Directing Groups
Cristofer Pezzetta1, Luis F Veiros2, Julie Oble1
1Institut Parisien de Chimie Moléculaire (IPCM), UMR 8232, Sorbonne Universités, UPMC Univ Paris 06, CNRS, 4 place Jussieu, 75005, Paris, France.
Abstract:
Furfural and related compounds are industrially relevant building blocks obtained from lignocellulosic biomass. To enhance the added value of these renewable resources, a Ru-catalyzed hydrofurylation of alkenes, involving a directed C-H activation at C3 of the furan ring, was developed. A thorough experimental study revealed that a bidentate amino-imine directing group enabled the desired coupling. Removal of the directing group occurred during the purification step, directly releasing the C3-functionalized furfurals. Development of the reaction as well as optimization and scope of the method were described. A mechanism was proposed on the basis of DFT calculations.
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