A simple and mild TBAT-catalyzed deoxygenative reduction of tertiary amides into amines
In organic synthesis, the reduction of amides into their corresponding amines is an important transformation, in particular in medicinal chemistry for the preparation of various substituted amines derivatives. Due to the low electrophilicity of the carbonyl carbon of the amide function, its reduction is difficult and required strong reducing agents and harsh reaction conditions. V. Vinayagam and Coll. published a fluoride ion catalyzed hydrosilylations using tetrabutylammonium triphenyldifluorosilicate (TBAT) and PhSiH3 (25 g around 200 €) as a hydride source to reduce amides to amines in THF at RT. [1] This chemoselective reduction is outlined in the Scheme below.
This methodology exhibits good substrates scope with around 30 examples, even if the authors have identified certain limitations. A mechanism is proposed for this reduction.
[1] V. Vinayagam et al., Org. Lett. 2023, 25, 4610-4614.
