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.

alcohol

glycerol

hydrogen borrowing

catalysis

amine

ruthenium

Författare

Anna Said Stålsmeden

Kemi och kemiteknik, Kemi och biokemi, Organisk kemi

José Luis Belmonte Vázquez

Chalmers University of Technology

Universidad de Guanajuato

Kim van Weerdenburg

Chalmers University of Technology

Rebecca Rae

AstraZeneca AB

Per-Ola Norrby

AstraZeneca AB

Nina Kann

Kemi och kemiteknik, Kemi och biokemi, Organisk kemi

ACS Sustainable Chemistry & Engineering

2168-0485 (eISSN)

Vol. 4 5730-5736

Drivkrafter

Hållbar utveckling

Fundament

Grundläggande vetenskaper

Styrkeområden

Livsvetenskaper och teknik

Materialvetenskap

Ämneskategorier

Organisk kemi

DOI

10.1021/acssuschemeng.6b01659