Synthesis of Renewable meta‐Xylylenediamine from Biomass‐Derived Furfural. Issue 33 (16th May 2018)

• Record Type: Journal Article
• Authors: Scodeller, Ivan; Mansouri, Samir; Morvan, Didier; Muller, Eric; de Oliveira Vigier, Karine; Wischert, Raphael; Jérôme, François
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 33(2018)
• Page Start: 10510
• Page End: 10514
• Publication Date: 2018-05-16
• Subjects: amination -- aromatics -- density functional calculations -- Diels–Alder reactions -- furfural; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201803828
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We report the synthesis of biomass‐derived functionalized aromatic chemicals from furfural, a building block nowadays available in large scale from low‐cost biomass. The scientific strategy relies on a Diels–Alder/aromatization sequence. By controlling the rate of each step, it was possible to produce exclusively the meta aromatic isomer. In particular, through this route, we describe the synthesis of renewably sourced meta ‐xylylenediamine (MXD). Transposition of this work to other furfural‐derived chemicals is also discussed and reveals that functionalized biomass‐derived aromatics (benzaldehyde, benzylamine, etc.) can be potentially produced, according to this route. Abstract : High‐value chemicals : Renewable meta ‐xylylenediamine has been produced at low temperatures from biomass‐derived furfural and acrylonitrile by using sequential Diels–Alder and base‐catalyzed aromatization reactions. The kinetic control of the aromatization step permitted the selective formation of the meta isomer.