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.

alcohol

ruthenium

catalysis

glycerol

hydrogen borrowing

amine

Author

Anna Said Stålsmeden

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Organic Chemistry

Jose Luis Belmonte Vazquez

Universidad de Guanajuato

Kim van Weerdenburg

Rebecca Rae

AstraZeneca AB

Per-Ola Norrby

AstraZeneca AB

Nina Kann

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Organic Chemistry

ACS Sustainable Chemistry & Engineering

2168-0485 (eISSN)

Vol. 4 10 5730-5736

Driving Forces

Sustainable development

Roots

Basic sciences

Areas of Advance

Life Science Engineering (2010-2018)

Materials Science

Subject Categories

Organic Chemistry

DOI

10.1021/acssuschemeng.6b01659

More information

Latest update

5/23/2018