Abstract
This chapter introduces the topic and scope of the book and principally concerns the basic preparation, physical and chemical properties of Ru-based oxidation catalysts, then summarising the catalytic oxidations which they accomplish. More detail on these is given in the succeeding four chapters. The major oxidants RuO4 (1.2.1), perruthenate [RuO4]− (1.3.1) – mainly TPAP, (nPr4N)[RuO4], ruthenate [RuO4]2− (1.4.1), trans-Ru(O)2(TMP) (1.4.2.5), RuCl2(PPh3)3 (1.9.3) and cis-RuCl2(dmso)4 (1.9.4) are covered in some detail, but many other catalysts are also discussed. In some cases brief comments are made on the mechanisms involved when data on these are given in the cited papers. There is also an Appendix (1.11) which gives brief details on the preparation of four ruthenium oxidation catalysts and selected model oxidations using them.
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Notes
- 1.
K. K. Klaus appears as C. Claus in the early German publications, which are cited here since they are more accessible than the Russian originals.
- 2.
Henceforth in most cases abbreviated as Ru.
- 3.
The hydrates RuO2.nH2O or RuCl3.nH2O are much more reactive than the anhydrous materials and are always used as such for oxidation catalysis. For brevity in this book, however, they will simply be referred to as RuO2 and RuCl3 respectively.
- 4.
As indicated in 1.1 above, this takes the form: Ru starting material/co-oxidant/solvent; temperatures are only indicated if not ambient. For brevity RuO2 and RuCl3 denote the hydrates RuO2.nH2O and RuCl3.nH2O.
- 5.
Oxidation of primary and secondary amines and of amides may be considered either as amine/amide or as alkane oxidations; for convenience they are considered here and in 5.1.1, 5.1.2 , cross-referenced in Ch. 4 .
- 6.
Oxidation of primary and secondary amines and of amides may be considered either as amine/amide or as alkane oxidations; for convenience they are considered here and in Ch. 5, cf. 5.1, 5.2 , cross-referenced in Ch. 4 .
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Appendix: Brief Resumé of Preparations of Ru Oxidants and Oxidation Reactions
Appendix: Brief Resumé of Preparations of Ru Oxidants and Oxidation Reactions
In this short section brief experimental details are given for the in situ preparations of RuO4, [RuO4]− and [RuO4]2−, the isolation of solid TPAP and of trans-Ru(O)2(bpy){IO3(OH)3}1.5H2O. There are also brief notes on specific oxidation procedures using these oxidants with which the author has had some experience. There are several good, practically explicit references in the literature to procedures with Ru oxidants, e.g. that by Haines [51, 202], Courtney [60] and by Lee and van der Engh [203].
All preparations, particularly those involving RuO4, should be carried out in a fume cupboard. It must be remembered that there is always a potential hazard involved in the handling of high oxidation state ruthenium compounds and of many of their co-oxidants.
1.1.1 Preparations of RuO4 In Situ for Oxidations
1.1.1.1 The Classic Sharpless Procedure for Oxidations with RuO4
Although this method is quite old it has stood the test of time, and is the basis of many modern oxidations with RuO4. Sharpless used it for oxidations of alcohols, ethers, aromatic rings and for alkene cleavage, so clearly it has a high range of applicability.
A representative experiment involved RuCl3 (0.005 g, 0.022 mmol) added to a solution of Na(IO4) (0.88 g, 4.1 mmol) in water (3 cm3), CCl4 (2 cm3) and CH3CN (2 cm3) with the substrate (1 mmol of E-decene in the example given); the mixture was stirred for 2 h [260]. This author recommends pre-dissolution of the RuCl3 in water (ca. 3 cm3) for some 12 h beforehand, and since Na(IO4) is not very soluble suggests the use of more water, e.g. 10 cm3.
1.1.1.2 Cleavage of Alkenes with RuO4
Cyclohexane is more environmentally acceptable than the more commonly-used CCl4. A recent cleavage of a mono-fluorinated alkene to a ketone was thus effected. The alkene (70 mg, 0.28 mmol) was dissolved in a mixture of acetonitrile (0.5 cm3) and cyclohexane (0.5 cm3) and treated with RuCl3.nH2O (0.05 g, 0.2 mmol) and Na(IO4) (0.24 g, 10 mmol) in water (1 cm3). The mixture was stirred for 1.5 h, the product extracted with diethylether and dried over MgSO4 [330]. Other examples, using RuCl3/aq. IO(OH)5/C6H12-CH3CN have been given [216].
1.1.2 Preparations and Use of [RuO4]−
1.1.2.1 Preparation of TPAP
The reagent is available commercially from a number of suppliers (this is not the case, of course, for RuO4), but the solid reagent may be simply and cheaply prepared in the laboratory. A pre-made aqueous solution of RuCl3 (0.13 g, 0.5 mmol) in water (5 cm3) is added to a solution of Na(BrO3) (6.0 g, 50 mmol) and anhydrous Na2(CO3) (1.58 g, 15 mmol) in water (20 cm3). These solutions are stirred together at room temperature until the typical green colour of [RuO4]− appears. An aqueous solution of (nPr4N)OH (0.1 g, 0.5 mmol) is then added with stirring; the deep green precipitate extracted into alcohol-free CH2Cl2 (50 cm3), the solution dried over anhydrous Na2(CO3), concentrated in vacuo and recrystallised from high-grade ethanol-free CCl4. This gives a yield of some 200 mg (ca. 0.5 mmol), sufficient for several catalytic oxidations. The preparation may be scaled up if required [213].
The salt is said to be prone to explosion at temperatures above 60°C although the author has not experienced this. It should not occur since TPAP is normally used at room temperatures, but it should be stored in a refrigerated desiccator.
1.1.2.2 Oxidations with TPAP
The recently published total synthesis of rapamycin involves several steps in which TPAP was used under a variety of conditions [173].
Primary alcohol to aldehyde. The alcohol (2 g, 7.9 mmol) was added to NMO (1.4 g, 11.0 mmol.) with oven-dried 4 Å powdered molecular sieves (PMS) in 1:1 CH2Cl2:CH3CN (40 cm3) and stirrecd for an hour before addition of TPAP (0.28 g, 0.79 mmol) and the green solution stirred for an hour before Celite filtration, in vacuo concentration and purification [173].
Secondary alcohol to ketone. As a step in the synthesis of avermectin B1a the alcohol (0.024 g, 0.04 mmol) in CH2Cl2 with TPAP (0.015 g, 0.004 mmol) and PMS (0.25 g) was mixed with NMO (0.005 g, 0.045 mmol) in CH2Cl2 (1 cm3) and stirred for 1 h under argon, filtered through a Florisil pad and extracted wioth EtOAc [95].
Diol to lactone. To the diol (0.09 g, 0.31 mmol) in CH2Cl2 (2.4 cm3) was added NMO (0.1 g, 0.92 mmol) and 4 Å PMS (0.11 g) and the mixture stirred for 10 min.; solid TPAP (0.01 g, 31.0 μmol) was added in portions, and after 1 h the reaction mixture was purified by flash chromatography [173].
1.1.2.3 Production of [RuO4]− in Aqueous Base: the [RuO4]− – (BrO3)− Reagent
This can be used for oxidations in aqueous base of primary alcohols, aldehydes, activated alkyl halides, cis-diols and nitroalkanes to carboxylic acids, and of secondary alcohols and secondary halides to ketones.
A solution of RuCl3 (0.003 g, 0.011 mmol) in water (1 cm3), prepared some 12 h in advance, is added with stirring to a solution of Na(BrO3) (1.2 g, 8 mmol) and anhydrous Na2(CO3) (0.8 g, 7.5 mmol) in water (10 cm3). This gives a yellow-green solution of [RuO4]− buffered to about pH 11; the electronic spectrum should have bands at 378 and 310 nm [213].
1.1.3 Preparations and Use of [RuO4]2−
This may be used for oxidations in aqueous base of primary alcohols, aldehydes, activated alkyl halides, cis-diols and nitroalakanes to carboxylic acids, and of secondary alcohols and secondary halides to ketones.
To a solution of RuCl3 (0.008 g, 0.03 mmol) in water (3 cm3), prepared some 12 h in advance, is added an aqueous solution of K2(S2O8) (0.7 g, 2.6 mmol) or the more soluble Na2(S2O8) in M KOH or NaOH (50 cm3) with stirring. This gives a deep orange-red solution of [RuO4]2− at pH 14; the electronic spectrum should have bands at 466 and 386 nm [213].
1.1.3.1 Oxidation of Amines with Aqueous [RuO4]2−
A useful example is the oxidative dehydrogenation of primary amines to nitriles. The amine (2 mmol) is added dropwise or in small portions to a vigorously stirred solutuion of [RuO4]2− prepared as above (100 cm3); the reaction is complete when the dark orange colour of [RuO4]2− reappears. The solution is extracted with diethylether (3x25 cm3), dried over MgSO4 and the ether removed [549].
1.1.4 Preparation of trans-Ru(O)2(bpy){IO3(OH)3}1.5H2O [568]
To a saturated aqueous solution of Na(IO4) (1.89 g, 9 mmol) is added RuO2.nH2O (0.5 g, 4 mmol) suspended in water (5 cm3). The resulting orange solution containing RuO4 is added to (bpy) (0.31 g, 2 cm3) in 1:1 acetone-water (20 cm3) and stirred for 5 min. The orange product is filtered off.
1.1.4.1 Epoxidation of Alkenes with trans-Ru(O)2(bpy){IO3(OH)3}1.5H2O
The complex (0.012 g, 0.02 mmol) is stirred in water (20 cm3) at 2°C for 15 min and the alkene (2 mmol) in CH2Cl2 (30 cm3) with Na(IO4) (3.0 g, 14 mmol) added, and the mixture stirred for 15 h at 2°C. By addition of aqueous M NaOH solution the pH is adjusted to 12 and the mixture extracted with CH2Cl2 (4 × 20 cm3), the extracts combined and dried over anhydrous MgSO4 and the sovent removed [568].
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Griffith, W.P. (2009). The Chemistry of Ruthenium Oxidation Complexes. In: Ruthenium Oxidation Complexes. Catalysis by Metal Complexes, vol 34. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-9378-4_1
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