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A number of reviews have described some aspects in comparison with other radical-based reducing agents, see: a) P. A. Baguley, J. C. Walton, Angew. Chem. 1998, 110, 3272;
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3Si or the so called super silyl group as a bulky substituent or a protecting group are numerous: for recent applications,
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3Si or the so called "super silyl" group as a bulky substituent or a protecting group are numerous: for recent applications,
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3SiH has also been reported. see: T. Ruhland, J. Torang, H. Pedersen, J. C. Madsen, K. S. Bang, Synthesis 2005, 1635.
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The recent debate on tris(trimetylsilyl)methane as reducing agent should be noted. It has clearly demonstrated (A. I. Longshaw, M. W. Carland, E. H. Krenske, M. L. Coote, M. S. Sherburn, Tetrahedron Lett. 2007, 48, 5585)
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The recent debate on tris(trimetylsilyl)methane as reducing agent should be noted. It has clearly demonstrated (A. I. Longshaw, M. W. Carland, E. H. Krenske, M. L. Coote, M. S. Sherburn, Tetrahedron Lett. 2007, 48, 5585)
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that this compound does not reduce organohalides under radical conditions as previously claimed (V. T. Perchyonok, Tetrahedron Lett. 2006, 47, 5163).
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that this compound does not reduce organohalides under radical conditions as previously claimed (V. T. Perchyonok, Tetrahedron Lett. 2006, 47, 5163).
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37
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0033484573
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Earlier work from Roberts' laboratory showed that trialkylsilanes reduce alkyl halides to the corresponding hydrocarbons in the presence of alkanethiols (the so-called polarity-reversal catalysis in the radical-chain reduction). He demonstrated that the key step in these reductions is the hydrogen transfer from silane to the thiyl radical, which is strongly endothermic and reversible. For a review, see: B. P. Roberts, Chem. Soc. Rev. 1999, 28, 25;
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a) Earlier work from Roberts' laboratory showed that trialkylsilanes reduce alkyl halides to the corresponding hydrocarbons in the presence of alkanethiols (the so-called polarity-reversal catalysis in the radical-chain reduction). He demonstrated that the key step in these reductions is the hydrogen transfer from silane to the thiyl radical, which is strongly endothermic and reversible. For a review, see: B. P. Roberts, Chem. Soc. Rev. 1999, 28, 25;
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3SiH costs Euro 80.2 for 5 mL and Euro 244.5 for 25 mL (FLUKA 2007/2008 catalog) and due to its stability and possibility for titration, could also be bought (or sold) in larger quantities that are more economical. To date, the efficiency of the silane in terms of reactivity and diastereoselectivity has no comparison with the results obtained with other less expensive radical-based reagents. The invaluable absence of toxicity, as compared to the tin reagents. both for the operator and for the use of the products, (e.g. in biological assays), considerably elevates the benefit/cost ratio.
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3SiH costs Euro 80.2 for 5 mL and Euro 244.5 for 25 mL (FLUKA 2007/2008 catalog) and due to its stability and possibility for titration, could also be bought (or sold) in larger quantities that are more economical. To date, the efficiency of the silane in terms of reactivity and diastereoselectivity has no comparison with the results obtained with other less expensive radical-based reagents. The invaluable absence of toxicity, as compared to the tin reagents. both for the operator and for the use of the products, (e.g. in biological assays), considerably elevates the benefit/cost ratio.
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