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Issue 31, 2019
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Carbohydrate-functionalized N-heterocyclic carbene Ru(II) complexes: synthesis, characterization and catalytic transfer hydrogenation activity

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Abstract

Three Ru complexes containing carbohydrate/N-heterocyclic carbene hybrid ligands were synthesized that were comprised of a triazolylidene coordination site and a directly linked per-acetylated glucosyl (5Glc) or galactosyl unit (5Gal), or a glycosyl unit linked through an ethylene spacer (6). Electrochemical and UV-vis analysis indicate only minor perturbation of the electronic configuration of the metal center upon carbohydrate installation. Deprotection of the carbohydrate was accomplished under basic conditions to afford complexes that were stable in solution over several hours, but decomposed in the solid state. Complexes 5 and 6 were used as pre-catalysts for transfer hydrogenation of ketones under basic conditions, i.e. conditions that lead to in situ deprotection of the carbohydrate entity. The carbohydrate directly influences the catalytic activity of the metal center. Remotely linked carbohydrates (complex 6) induce significantly lower catalytic activity than directly linked carbohydrates (complexes 5Glc, 5Gal), while unfunctionalized triazolylidenes are an order of magnitude more active. These observations and substrate variations strongly suggest that substrate bonding is rate-limiting for transfer hydrogenation in these hybrid carbohydrate/triazolylidene systems.

Graphical abstract: Carbohydrate-functionalized N-heterocyclic carbene Ru(ii) complexes: synthesis, characterization and catalytic transfer hydrogenation activity

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Publication details

The article was received on 20 Jun 2019, accepted on 01 Jul 2019 and first published on 05 Jul 2019


Article type: Paper
DOI: 10.1039/C9DT02614B
Dalton Trans., 2019,48, 11838-11847
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    Carbohydrate-functionalized N-heterocyclic carbene Ru(II) complexes: synthesis, characterization and catalytic transfer hydrogenation activity

    J. P. Byrne, P. Musembi and M. Albrecht, Dalton Trans., 2019, 48, 11838
    DOI: 10.1039/C9DT02614B

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