Efficient alkylation of ketones with primary alcohols catalyzed by ruthenium(II)/P,N ligand complexes

Shi Yuan Liu, Lin Yan Xu, Chun Yu Liu, Zhi Gang Ren, David James Young, Jian Ping Lang

Research output: Contribution to journalArticle

Abstract

An efficient catalytic system containing [RuCl26-p-cymene)]2 and one P,N ligand, N-diphenylphosphino-2-aminopyridine (L1) was loaded in catalyzing the alkylation of ketones with primary alcohols for a diverse array of substrates. Other five P,N ligands based on pyridin-2-amine and pyrimidin-2-amine were also examined in this reaction to explore the influence of steric hindrance and electronic effects. Monitoring by 1H NMR and ESI-MS reveals a stable cationic L1-coordinated ruthenium hydride intermediate, identified as [Ru(η6-p-cymene)(κ2-L1)H]+. Organic intermediates consistent with a three-step dehydrogenation, alkylation and hydrogenation pathway were also observed. The final step in this reaction, the ruthenium-catalysed transfer hydrogenation reduction of α,β-unsaturated ketone with benzyl alcohol was performed separately.

Original languageEnglish
Pages (from-to)2374-2381
Number of pages8
JournalTetrahedron
Volume73
Issue number17
DOIs
Publication statusPublished - 27 Apr 2017
Externally publishedYes

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