Rhenium-Catalyzed Reduction of Carboxylic Acids with Hydrosilanes
Re2(CO)10 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 Et3SiH (2.2 equiv), aromatic analogues required more drastic conditions (Re2(CO)10 5 mol %, Ph2MeSiH 4.0 equiv) to afford the corresponding aldehydes after acid treatment.
Selective reduction of carboxylic acids to aldehydes through manganese catalysed hydrosilylation
The direct reduction of carboxylic acids to disilylacetals was achieved through a manganese catalyzed hydrosilylation reaction in the presence of triethylsilane under mild conditions, at r.t. and under UV irradiation (350 nm). The aldehydes were obtained in good to excellent yields after acidic hydrolysis.
Selective reduction of carboxylic acids to aldehydes catalyzed by B(C 6F5)3
B(C6F5)3 efficiently catalyzes hydrosilylation of aliphatic and aromatic carboxylic acids to produce disilyl acetals under mild conditions. Catalyst loadings can be as low as 0.05 mol %, and bulky tertiary silanes are favored to give selectively the acetals. Acidic workup of the disilyl acetals results in the formation of aldehydes in good to excellent yields.
Bezier, David,Park, Sehoon,Brookhart, Maurice
supporting information
p. 496 - 499
(2013/03/29)
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