Ruthenium-catalyzed deaminative hydrogenation of amino nitriles

• Verfasst von: Calleja Ramos, Pilar [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Ruthenium-catalyzed deaminative hydrogenation of amino nitriles
• Titelzusatz: direct access to 1,2-amino alcohols
• Verf.angabe: Pilar Calleja, Martin Ernst, A. Stephen K. Hashmi, and Thomas Schaub
• E-Jahr: 2019
• Jahr: 08 March 2019
• Umfang: 6 S.
• Fussnoten: Version of record online: April 17, 2019 ; Gesehen am 07.11.2019
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2019
• Band/Heft Quelle: 25(2019), 40, Seite 9498-9503
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201900531
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: amino alcohols
• Sach-SW: deamination
• Sach-SW: hydrogenation
• Sach-SW: nitriles
• Sach-SW: ruthenium
• K10plus-PPN: 168142374X

Abstract

A new approach for the efficient and highly selective synthesis of 1,2-amino alcohols by direct reductive hydrolysis of N-formyl-protected α-amino nitriles is reported. The commercially available RuHCl(CO)(PPh3)3 complex was found to be a suitable catalyst for this operationally simple protocol, in which no stoichiometric amounts of undesired metal waste are generated. The deaminative hydrogenation is performed at 55 bar of H2, using a 6:1 mixture of 1,4-dioxane/water as solvent. In addition, hydroxymethyl alcohols were prepared from cyanoketones under very similar conditions.