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Glycerol Upgrading via Hydrogen Borrowing: Direct Ruthenium- Catalyzed Amination of the Glycerol Derivative Solketal

Anna Said Stålsmeden (Institutionen för kemi och kemiteknik, Organisk kemi) ; José Luis Belmonte Vázquez ; Kim van Weerdenburg ; Rebecca Rae ; Per-Ola Norrby ; Nina Kann (Institutionen för kemi och kemiteknik, Organisk kemi)
ACS Sustainable Chemistry & Eneering Vol. 4 (2016), 10, p. 5730-5736.
[Artikel, refereegranskad vetenskaplig]

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.

Nyckelord: glycerol, catalysis, hydrogen borrowing, ruthenium, alcohol, amine



Denna post skapades 2016-10-03. Senast ändrad 2016-12-09.
CPL Pubid: 242836

 

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Institutioner (Chalmers)

Institutionen för kemi och kemiteknik, Organisk kemi

Ämnesområden

Organisk syntes

Chalmers infrastruktur