Olefin Metathesis Reaction in Water and in Air Improved by Supramolecular Additives.
A range of water-immiscible commercially available Grubbs-type precatalysts can be used in ring-closing olefin metathesis reaction in high yields. The synthetic transformation is possible in pure water under ambient conditions. Sulfocalixarenes can help to boost the reactivity of the metathesis reaction by catalyst activation, improved mass transfer, and solubility of reactants in the aqueous reaction media. Additionally, the use of supramolecular additives allows lower catalyst loadings, but still high activity in pure water under aerobic conditions.
Organic Chemistry 1, Department of Chemistry and Pharmacy, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Henkestraße 42, D-91054 Erlangen, Germany. jasmine.tomasek@fau.de.
Jasmine
J
Tomasek
Organic Chemistry 1, Department of Chemistry and Pharmacy, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Henkestraße 42, D-91054 Erlangen, Germany. m.b.sessler@web.de.
Miriam
M
Seßler
Faculty of Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany. harald.groeger@uni-bielefeld.de.
Harald
H
Gröger
Organic Chemistry 1, Department of Chemistry and Pharmacy, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Henkestraße 42, D-91054 Erlangen, Germany. juergen.schatz@fau.de.
Jürgen
J
Schatz
D000388:Air; D000475:Alkenes / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D014867:Water / Q000737:chemistry
D000475:Alkenes; D012997:Solvents; D014867:Water
C-C coupling; aqueous metathesis; supramolecular chemistry