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.
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Stockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, SE-10691 Stockholm, SwedenStockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Bartoszewicz, Agnieszka
Miera, Greco Gonzalez
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Stockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, SE-10691 Stockholm, SwedenStockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Miera, Greco Gonzalez
Marcos, Rocio
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Stockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, SE-10691 Stockholm, SwedenStockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Marcos, Rocio
Norrby, Per-Ola
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Gothenburg Univ, Chem & Mol Biol Dept, SE-41296 Gothenburg, Sweden
AstraZeneca, Pharmaceut Dev, SE-43183 Molndal, SwedenStockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Norrby, Per-Ola
Martin-Matute, Belen
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Stockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, SE-10691 Stockholm, SwedenStockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
机构:
Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Bartoszewicz, Agnieszka
Marcos, Rocio
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Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Marcos, Rocio
Sahoo, Suman
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Stockholm Univ, Dept Mat & Environm Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Sahoo, Suman
Inge, A. Ken
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Stockholm Univ, Dept Mat & Environm Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Inge, A. Ken
Zou, Xiaodong
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Stockholm Univ, Dept Mat & Environm Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Zou, Xiaodong
Martin-Matute, Belen
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Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
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Stockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, SE-10691 Stockholm, SwedenStockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Bartoszewicz, Agnieszka
Miera, Greco Gonzalez
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Stockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, SE-10691 Stockholm, SwedenStockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Miera, Greco Gonzalez
Marcos, Rocio
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Stockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, SE-10691 Stockholm, SwedenStockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Marcos, Rocio
Norrby, Per-Ola
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Gothenburg Univ, Chem & Mol Biol Dept, SE-41296 Gothenburg, Sweden
AstraZeneca, Pharmaceut Dev, SE-43183 Molndal, SwedenStockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Norrby, Per-Ola
Martin-Matute, Belen
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机构:
Stockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, SE-10691 Stockholm, SwedenStockholm Univ, Organ Chem Dept, Arrhenius Lab, SE-10691 Stockholm, Sweden
机构:
Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Bartoszewicz, Agnieszka
Marcos, Rocio
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机构:
Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Marcos, Rocio
Sahoo, Suman
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机构:
Stockholm Univ, Dept Mat & Environm Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Sahoo, Suman
Inge, A. Ken
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机构:
Stockholm Univ, Dept Mat & Environm Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Inge, A. Ken
Zou, Xiaodong
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Stockholm Univ, Dept Mat & Environm Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Zou, Xiaodong
Martin-Matute, Belen
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机构:
Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, SwedenStockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden