Reduction Over Condensation of Carbonyl Compounds Through a Transient Hemiaminal Intermediate Using Hydrazine

Abstract

Reduction of carbonyl moieties to the corresponding alcohol using simply hydrazine hydrate has been considerably unfeasible until now due to the wellknown condensation reaction. However, herein, we report that using an excess of 20fold equivalents, the reduction proceeds in excellent yields. 1 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.

Selective reduction of nitroarenes using Ru/C and CaH2

“…21 In 2015 the group of Métay and Lemaire reported the reductive alkylation and reductive amination of carbonyl compounds using CaH 2 but this time in combination with supported heterogeneous catalysts of Pd/C and Pt/C respectively. 22 Based on these reports and as part of our continuing interest in the reduction of organic functionalities, 23 we decided to explore the suitability of this hydride for the reduction of nitroarenes. Herein we report the highly selective reduction of aromatic and heteroaromatic nitro compounds using Ru/C and CaH 2 .…”