A green route to nitrogen-containing groups: the acrylonitrile cross-metathesis and applications to plant oil derivatives

• Published in: Green chemistry : an international journal and green chemistry resource : GC Vol. 13; no. 9; pp. 2258 - 2271
• Main Authors: XIAOWEI MIAO, DIXNEUF, Pierre H, FISCHMEISTER, Cedric, BRUNEAU, Christian
• Format: Journal Article
• Language: English
• Published: Cambridge Royal Society of Chemistry 01.01.2011
• Subjects: Byproducts; Catalysis; Catalysts: preparations and properties; Chemistry; Exact sciences and technology; General and physical chemistry; Lipids; Organic chemistry; Preparations and properties; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Catalytic reaction; Acrylonitrile; Mild operating conditions; Bifunctional compound; Ethylene; Metathesis; Glycerol; Lipids; Vegetable oil; Review; Wasteless technology; Fatty acids; Complexes; Alkene; Preparation; Cross reaction; Green chemistry; Catalysis; Chemical synthesis; By product; Catalyst; Ethylenic compound
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c1gc15377c

Acrylonitrile has become a renewable material arising from glycerol. It can now be used as an available key product to introduce a nitrogen-containing functionality into a molecule by cross-metathesis. This review successively presents the developments of catalytic cross-metathesis of acrylonitrile with functional alkenes: (i) the first steps of cross-metathesis of acrylonitrile with simple terminal alkenes, of which the successes were linked to the progressive discoveries of efficient alkene metathesis catalysts, (ii) some contributions of this catalytic reaction to synthesis of complex molecules and (iii) the access to renewable [small alpha],[small omega]-bifunctional compounds by acrylonitrile cross-metathesis with fatty acid derivatives, arising from plant oils. The combination of the renewable acrylonitrile and fatty acid derivatives, by catalysis under mild conditions with only ethylene as a by-product, constitutes a clear contribution to green chemistry for the production of useful intermediates.