Direct Synthesis of Symmetrical Azines from Alcohols and Hydrazine Catalyzed by a Ruthenium Pincer Complex: Effect of Hydrogen Bonding
datasetposted on 17.11.2016, 00:00 by Jonathan O. Bauer, Gregory Leitus, Yehoshoa Ben-David, David Milstein
Azines (2,3-diazabuta-1,3-dienes) are a widely used class of compounds with conjugated CN double bonds. Herein, we present a direct synthesis of azines from alcohols and hydrazine hydrate. The reaction, catalyzed by a ruthenium pincer complex, evolves dihydrogen and can be run in a base-free version. The dehydrogenative coupling of benzylic and aliphatic alcohols led to good conversions and yields. Spectroscopic evidence for a hydrazine-coordinated dearomatized ruthenium pincer complex was obtained. Isolation of a supramolecular crystalline compound provided evidence for the important role of hydrogen bonding networks under the reaction conditions.
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reaction conditionsdehydrogenativehydrazine hydratesupramolecularHereinaliphatic alcoholsruthenium pincerRuthenium Pincer ComplexdihydrogenBondingrolediazabutaSymmetrical AzinesIsolationconversionhydrazine-coordinated dearomatized ruthenium pincercompoundbase-free versionbenzylicSpectroscopic evidenceHydrazine CatalyzedDirect Synthesissynthesisyieldbond