5 years ago

Murai Reaction on Furfural Derivatives Enabled by Removable N,N′-Bidentate Directing Groups

Murai Reaction on Furfural Derivatives Enabled by Removable N,N′-Bidentate Directing Groups
Cristofer Pezzetta, Giovanni Poli, Julie Oble, Luis F. Veiros
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. Furfural activated: A Ru0-catalyzed Murai reaction of furfural derivatives, enabled by N,N′-bidentate directing groups, is developed. This C−H activation process provides a straightforward valorization pathway for a major class of lignocellulose-derived biomass substrates. The importance of the directing group design is evaluated, and the reaction mechanism is elucidated by using DFT calculations.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701850

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