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      Selective conversion of alcohols in water to carboxylic acids by in situ generated ruthenium trans dihydrido carbonyl PNP complexes

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          Abstract

          In this work, we present a mild method for direct conversion of primary alcohols into carboxylic acids with the use of water as an oxygen source.

          Abstract

          In this work, we present a mild method for direct conversion of primary alcohols into carboxylic acids with the use of water as an oxygen source. Applying a ruthenium dihydrogen based dehydrogenation catalyst for this cause, we investigated the effect of water on the catalytic dehydrogenation process of alcohols. Using 1 mol% of the catalyst we report up to high yields. Moreover, we isolated key intermediates which most likely play a role in the catalytic cycle. One of the intermediates was identified as a trans dihydrido carbonyl complex which is generated in situ in the catalytic process.

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          Direct synthesis of amides from alcohols and amines with liberation of H2.

          Chidambaram Gunanathan, Yehoshoa Ben-David, David Milstein (2007)
          Given the widespread importance of amides in biochemical and chemical systems, an efficient synthesis that avoids wasteful use of stoichiometric coupling reagents or corrosive acidic and basic media is highly desirable. We report a reaction in which primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only products) in high yields and high turnover numbers. This reaction is catalyzed by a ruthenium complex based on a dearomatized PNN-type ligand [where PNN is 2-(di-tert-butylphosphinomethyl)-6-(diethylaminomethyl)pyridine], and no base or acid promoters are required. Use of primary diamines in the reaction leads to bis-amides, whereas with a mixed primary-secondary amine substrate, chemoselective acylation of the primary amine group takes place. The proposed mechanism involves dehydrogenation of hemiaminal intermediates formed by the reaction of an aldehyde intermediate with the amine.
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            Low-temperature aqueous-phase methanol dehydrogenation to hydrogen and carbon dioxide.

            Martin L. Nielsen, Elisabetta Alberico, Wolfgang Baumann … (2013)
            Hydrogen produced from renewable resources is a promising potential source of clean energy. With the help of low-temperature proton-exchange membrane fuel cells, molecular hydrogen can be converted efficiently to produce electricity. The implementation of sustainable hydrogen production and subsequent hydrogen conversion to energy is called "hydrogen economy". Unfortunately, its physical properties make the transport and handling of hydrogen gas difficult. To overcome this, methanol can be used as a material for the storage of hydrogen, because it is a liquid at room temperature and contains 12.6 per cent hydrogen. However, the state-of-the-art method for the production of hydrogen from methanol (methanol reforming) is conducted at high temperatures (over 200 degrees Celsius) and high pressures (25-50 bar), which limits its potential applications. Here we describe an efficient low-temperature aqueous-phase methanol dehydrogenation process, which is facilitated by ruthenium complexes. Hydrogen generation by this method proceeds at 65-95 degrees Celsius and ambient pressure with excellent catalyst turnover frequencies (4,700 per hour) and turnover numbers (exceeding 350,000). This would make the delivery of hydrogen on mobile devices--and hence the use of methanol as a practical hydrogen carrier--feasible.
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              A homogeneous transition metal complex for clean hydrogen production from methanol-water mixtures.

              Rafael E Rodríguez-Lugo, Mónica Trincado, Matthias Vogt … (2013)
              The development of an efficient catalytic process that mimics the enzymatic function of alcohol dehydrogenase is critical for using biomass alcohols for both the production of H2 as a chemical energy carrier and fine chemicals under waste-free conditions. Dehydrogenation of alcohol-water mixtures into their corresponding acids with molecular hydrogen as the sole by-product from the reaction can be catalysed by a ruthenium complex with a chelating bis(olefin) diazadiene ligand. This complex, [K(dme)2][Ru(H)(trop2dad)], stores up to two equivalents of hydrogen intramolecularly, and catalyses the production of H2 from alcohols in the presence of water and a base under homogeneous conditions. The conversion of a MeOH-H2O mixture proceeds selectively to CO2/H2 gas formation under neutral conditions, thereby allowing the use of the entire hydrogen content (12% by weight). Isolation and characterization of the ruthenium complexes from these reactions suggested a mechanistic scenario in which the trop2dad ligand behaves as a chemically 'non-innocent' co-operative ligand.
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                Author and article information

                Journal
                Journal ID (publisher-id): ICHBD9
                Title: Dalton Trans.
                Abbreviated Title: Dalton Trans.
                Publisher: Royal Society of Chemistry (RSC)
                ISSN (Print): 1477-9226
                ISSN (Electronic): 1477-9234
                Publication date Created: 2014
                Publication date (Print): 2014
                Volume: 43
                Issue: 46
                Pages: 17248-17254
                Article
                DOI: 10.1039/C4DT01634C
                PubMed ID: 25019331
                SO-VID: 2ddc0c11-b4e7-4feb-a630-4b94f86236a2
                Copyright © © 2014
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