Iron oxide catalyzed reduction of acid chlorides to aldehydes with hydrosilanes

Abstract

Iron-catalyzed reduction of acid chlorides to the corresponding aldehydes with a hydrosilane as a reducing agent has been developed. A simple mixture of a commercially available iron oxide (FeO) and tris(2,4,6-trimethoxyphenyl)phosphine (TMPP) as a catalyst realized the reduction of acid chlorides to the corresponding aldehydes under mild reaction conditions.

Iron-catalyzed reduction of carboxylic and carbonic acid derivatives

“…Tsuji et al reported that an iron catalyst, generated in situ from iron oxide (FeO) in the presence of phenyl silane as reducing agent and tris(2,4,6-trimethoxyphenyl)phosphine, was able to reduce at room temperature various aliphatic acyl chlorides into the corresponding aldehydes in moderate yields (36-58%) [32]. No other triaryl phosphine, or trialkyl phosphine improved the catalytic activity.…”

Iron Catalysis in Organic Synthesis

“…In 2014, Tsuji and co-workers described a procedure for a Rosenmund-like reduction of carboxylic acid chlorides with phenylsilane to provide aldehydes in moderate yields . The transformation was performed in toluene at 60–120 °C using iron(II) oxide in combination with tris(2,4,6-trimethylphenyl)phosphine (TMPP) as catalytic system.…”

Iron Catalysis in Reduction and Hydrometalation Reactions

“…Noticeably, aldehydes were obtained starting from more reactive acyl chlorides using a catalytic system generated from FeO (20 mol %) and tris­(2,4,6-trimethoxyphenyl)­phosphine (TMPP, 5.0 mol %) in the presence of PhSiH 3 (1.12 equiv) in toluene at 60–120 °C for 20 h …”

“…A final reductive elimination produced the silylated acetal and regenerated the unsaturated iron(0) active species. 369 Noticeably, aldehydes were obtained starting from more reactive acyl chlorides using a catalytic system generated from FeO (20 mol %) and tris(2,4,6-trimethoxyphenyl)phosphine (TMPP, 5.0 mol %) in the presence of PhSiH 3 (1.12 equiv) in toluene at 60−120 °C for 20 h. 371 3.4.4. Carboxylic Acids.…”