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

Cristofer Pezzetta; Luis F Veiros; Julie Oble; Giovanni Poli

doi:10.1002/chem.201701850

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

Chemistry. 2017 Jun 22;23(35):8385-8389. doi: 10.1002/chem.201701850. Epub 2017 May 30.

Authors

Cristofer Pezzetta¹, Luis F Veiros², Julie Oble¹, Giovanni Poli¹

Affiliations

¹ Institut Parisien de Chimie Moléculaire (IPCM), UMR 8232, Sorbonne Universités, UPMC Univ Paris 06, CNRS, 4 place Jussieu, 75005, Paris, France.
² Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001, Lisbon, Portugal.

PMID: 28445630
DOI: 10.1002/chem.201701850

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.

Keywords: C−H activation; aldimines; alkenes; furfural; ruthenium.