Iridium-catalyzed chemoselective transfer hydrogenation of α, β-unsaturated ketones to saturated ketones in water

A chemoselective iridium-catalyzed transfer hydrogenation of a, (3-unsaturated ketones was realized in water. The C=C double bonds of 2-benzylidene indanones and analogues were hydrogenated exclusively catalyzed by an iridium complex (0.1 mol%) bearing a pyridine-imidazoline ligand, using a mixture of formic acid/triethyl amine (molar ratio: 5/2) as a hydrogen source in water. A series of 2-benzyl indanones and analogues were obtained with good functional group tolerance and good yields. The practicability of this approach is also demonstrated by a gram-scale synthesis. (C) 2022 Elsevier Ltd. All rights reserved.

Automated summary

A chemoselective iridium-catalyzed transfer hydrogenation of α,β-unsaturated ketones was achieved in water, resulting in a series of 2-benzyl indanones and analogues with high yields and good functional group tolerance. The practicality of this approach was demonstrated through gram-scale synthesis.