Glycerol Upgrading via Hydrogen Borrowing: Direct Ruthenium- Catalyzed Amination of the Glycerol Derivative Solketal
Artikel i vetenskaplig tidskrift, 2016
Hydrogen borrowing provides an efficient and atom economical method for carbon–nitrogen and carbon–carbon bond formation from alcohol precursors. Glycerol is a renewable nontoxic polyol and a potential precursor to small functional organic molecules. We here report the direct amination of solketal, a 1,2-hydroxy-protected derivative of glycerol, via ruthenium-catalyzed hydrogen borrowing, affording up to 99% conversion and 92% isolated yield using [Ru(p-cymene)Cl2]2 as the catalyst precursor. The synthesis of an antitussive agent in 86% overall yield from solketal was also demonstrated using this methodology.
amine
catalysis
hydrogen borrowing
alcohol
ruthenium
glycerol
Författare
Anna Said Stålsmeden
Chalmers, Kemi och kemiteknik, Kemi och biokemi
José Luis Belmonte Vázquez
Chalmers University of Technology
Universidad de Guanajuato
Kim van Weerdenburg
Chalmers University of Technology
Rebecca Rae
AstraZeneca Sweden
Per-Ola Norrby
AstraZeneca Sweden
Nina Kann
Chalmers, Kemi och kemiteknik, Kemi och biokemi
ACS Sustainable Chemistry & Engineering
2168-0485 (eISSN)
Vol. 4 10 5730-5736Drivkrafter
Hållbar utveckling
Fundament
Grundläggande vetenskaper
Styrkeområden
Livsvetenskaper och teknik (2010-2018)
Materialvetenskap
Ämneskategorier (SSIF 2011)
Organisk kemi
DOI
10.1021/acssuschemeng.6b01659