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

Vilches-Herrera, Marcelo; Gallardo-Fuentes, Sebastian; Aravena-Opitz, Mauricio; Yanez-Sanchez, Mauricio; Jiao, Haijun; Holz, Jens; Boerner, Armin; Luhr, Susan

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-1 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.

Más información

Título según WOS: Reduction Over Condensation of Carbonyl Compounds Through a Transient Hemiaminal Intermediate Using Hydrazine
Título de la Revista: JOURNAL OF ORGANIC CHEMISTRY
Volumen: 85
Número: 14
Editorial: American Chemical Society
Fecha de publicación: 2020
Página de inicio: 9213
Página final: 9218
DOI:

10.1021/ACS.JOC.0C01212

Notas: ISI