Rhenium-Catalyzed Reduction of Carboxylic Acids with Hydrosilanes

Duo Wei (1, 2) , Ruqaya Buhaibeh (2) , Yves Canac (2) , Jean-Baptiste Sortais (3, 2)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LCC - Laboratoire de chimie de coordination
3 IUF - Institut Universitaire de France

Re(CO) efficiently catalyzes the direct reduction of various carboxylic acids under mild conditions (rt, irradiation 350 or 395 nm). While aliphatic carboxylic acids were readily converted to the corresponding disilylacetals with low catalyst loading (0.5 mol %) in the presence of EtSiH (2.2 equiv), aromatic analogues required more drastic conditions (Re(CO) 5 mol %, PhMeSiH 4.0 equiv) to afford the corresponding aldehydes after acid treatment.

Keywords: Organic acids; Redox reactions; Aldehydes; CatalystsIrradiation

Domains: Chemical Sciences

Duo Wei, Ruqaya Buhaibeh, Yves Canac, Jean-Baptiste Sortais. Rhenium-Catalyzed Reduction of Carboxylic Acids with Hydrosilanes. Organic Letters, 2019, 21 (19), pp.7713-7716. ⟨10.1021/acs.orglett.9b02449⟩. ⟨hal-02307033⟩