Issue 6, 2017

Cooperative interplay between a flexible PNN-Ru(ii) complex and a NaBH4 additive in the efficient catalytic hydrogenation of esters

Abstract

A catalyst loading of between 0.001–0.05 mol% of the PNN-bearing ruthenium(II) complex [fac-PNN]RuH(PPh3)(CO) (PNN = 8-(2-diphenylphosphinoethyl)amidotrihydroquinoline), in combination with 5 mol% NaBH4, efficiently catalyzes the hydrogenation of esters to their corresponding alcohols under mild pressures of hydrogen. Both aromatic and aliphatic esters can be converted with high values of TON or TOF achievable. Mechanistic investigations using both DFT calculations and labeling experiments highlight the cooperative role of NaBH4 in the catalysis while the catalytically active species has been established as trans-dihydride [mer-PNHN]RuH2(CO) (PNHN = 8-(2-diphenylphosphinoethyl)aminotrihydroquinoline). The stereo-structure of the PNHN-ruthenium species greatly affects the activity of the catalyst, and indeed the cis-dihydride isomer [fac-PNHN]RuH2(CO) is unable to catalyze the hydrogenation of esters until ligand reorganization occurs to give the trans isomer.

Graphical abstract: Cooperative interplay between a flexible PNN-Ru(ii) complex and a NaBH4 additive in the efficient catalytic hydrogenation of esters

Supplementary files

Article information

Article type
Paper
Submitted
17 Nov 2016
Accepted
01 Feb 2017
First published
02 Feb 2017

Catal. Sci. Technol., 2017,7, 1297-1304

Cooperative interplay between a flexible PNN-Ru(II) complex and a NaBH4 additive in the efficient catalytic hydrogenation of esters

Z. Wang, X. Chen, B. Liu, Q. Liu, G. A. Solan, X. Yang and W. Sun, Catal. Sci. Technol., 2017, 7, 1297 DOI: 10.1039/C6CY02413K

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