Reduction Over Condensation of Carbonyl Compounds Through a Transient Hemiaminal Intermediate Using Hydrazine.
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2020
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Abstract
Reduction of carbonyl moieties to the corresponding alcohol using simply hydrazine hydrate has been considerably unfeasible until now due to the well-known condensation reaction. However, herein, we report that using an excess of 20-fold equivalents, the reduction proceeds in excellent yields. H NMR study of the reaction and density functional theory (DFT) calculations indicate that the final fate of the hemiaminal intermediate is crucial to obtain the alcohol or the hydrazone.| Reference Key |
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| Authors | Vilches-Herrera, Marcelo;Gallardo-Fuentes, Sebastián;Aravena-Opitz, Mauricio;Yáñez-Sánchez, Mauricio;Jiao, Haijun;Holz, Jens;Börner, Armin;Lühr, Susan; |
| Journal | The Journal of organic chemistry |
| Year | 2020 |
| DOI | 10.1021/acs.joc.0c01212 |
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