Glycerol Upgrading via Hydrogen Borrowing: Direct Ruthenium- Catalyzed Amination of the Glycerol Derivative Solketal
Journal article, 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
Author
Anna Said Stålsmeden
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
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, Chemistry and Chemical Engineering, Chemistry and Biochemistry
ACS Sustainable Chemistry & Engineering
2168-0485 (eISSN)
Vol. 4 10 5730-5736Driving Forces
Sustainable development
Roots
Basic sciences
Areas of Advance
Life Science Engineering (2010-2018)
Materials Science
Subject Categories (SSIF 2011)
Organic Chemistry
DOI
10.1021/acssuschemeng.6b01659