Extending the Scope of the B(C6F5)3‐Catalyzed CN Bond Reduction: Hydrogenation of Oxime Ethers and Hydrazones |
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| Authors: | Jens Mohr Digvijay Porwal Dr. Indranil Chatterjee Prof. Dr. Martin Oestreich |
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| Affiliation: | Institut für Chemie, Technische Universit?t Berlin, Stra?e des 17.?Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu‐berlin.de |
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| Abstract: | The B(C6F5)3‐catalyzed hydrogenation is applied to aldoxime triisopropylsilyl ethers and hydrazones bearing an easily removable phthaloyl protective group. The C?N reduction of aldehyde‐derived substrates (oxime ethers and hydrazones) is enabled by using 1,4‐dioxane as the solvent known to participate as the Lewis‐basic component in FLP‐type heterolytic dihydrogen splitting. More basic ketone‐derived hydrazones act as Lewis bases themselves in the FLP‐type dihydrogen activation and are therefore successfully hydrogenated in nondonating toluene. The difference in reactivity between aldehyde‐ and ketone‐derived substrates is also reflected in the required catalyst loading and dihydrogen pressure. |
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| Keywords: | boron homogeneous catalysis hydrogenation Lewis acids reduction |
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