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

doi:10.1016/j.tet.2017.03.022

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

Journal article

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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 and Jian-Ping Lang

Tetrahedron, Vol.73(17), pp.2374-2381

2017

DOI: https://doi.org/10.1016/j.tet.2017.03.022

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Abstract

P,N hybrid ligand

ruthenium hydride

alkylation

alcohol

ruthenium(II)

An efficient catalytic system containing [RuCl2(η6-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.

Details

Title: Efficient alkylation of ketones with primary alcohols catalyzed by ruthenium(II)/P,N ligand complexes
Authors: Shi-Yuan Liu (Author) - Soochow University, People's Republic of China
Lin-Yan Xu (Author) - Soochow University, People's Republic of China
Chun-Yu Liu (Author) - Soochow University, People's Republic of China
Zhi-Gang Ren (Author) - Soochow University, People's Republic of China
David James Young (Author) - University of the Sunshine Coast - Faculty of Science, Health, Education and Engineering
Jian-Ping Lang (Author) - Soochow University, People's Republic of China
Publication details: Tetrahedron, Vol.73(17), pp.2374-2381
Publisher: Pergamon
Date published: 2017
DOI: 10.1016/j.tet.2017.03.022
ISSN: 0040-4020
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99450340202621
Output Type: Journal article

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Collaboration types: Domestic collaboration; International collaboration
Web Of Science research areas: Chemistry, Organic