Reduction of carbonyl groups by high-valent rhenium oxides

Beatriz Royo; Carlos C. Romão

doi:10.1016/j.molcata.2005.04.030

Reduction of carbonyl groups by high-valent rhenium oxides

Beatriz Royo, Carlos C. Romão

Instituto de Tecnologia Química e Biológica António Xavier (ITQB)

Research output: Contribution to journal › Article › peer-review

64 Citations (Scopus)

Abstract

The oxo-rhenium complexes [Re₂O₇] (1), [ReMeO ₃] (2), [Re(η⁵-C₅H₅)O ₃] (3), [ReO₂Cl(DMSO)₂] (4), [ReO ₂Me(PhCCPh)] (5), and [ReOCl₃(PPh₃) ₂] (6) catalyze the hydrosilylation of aliphatic and aromatic aldehydes with dimethylphenylsilane in C₆D₆ solutions. Compound 1 catalyzes the hydrosilylation of aldehydes at room temperature, affording the corresponding silyl ethers in good yield, but is ineffective as ketone hydrosilylation catalyst. The reactions of aldehydes and ketones with dimethylphenylsilane using compounds 2-6 as catalysts, require heating at 80 °C. The scope of rhenium oxides-mediated hydrosilylation with a variety of aldehydes and ketones has been studied. Methyltrioxorhenium(VII) (2) and oxotrichlorobis(triphenylphosphine)rhenium(V) (6) shown to be the most active and versatile catalysts for the hydrosilylation of aliphatic and aromatic aldehydes and also ketones. The dioxo-rhenium derivatives [ReO ₂Me(PhCCPh)] and [ReO₂Cl(DMSO)₂] also catalyze the reaction of dimethylphenylsilane and aldehydes, although longer reaction times were required.

Original language	English
Pages (from-to)	107-112
Number of pages	6
Journal	Journal of Molecular Catalysis A: Chemical
Volume	236
Issue number	1-2
DOIs	https://doi.org/10.1016/j.molcata.2005.04.030
Publication status	Published - 18 Jul 2005

Keywords

Catalysis
Hydrosilylation
Oxo
Rhenium

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title = "Reduction of carbonyl groups by high-valent rhenium oxides",

abstract = "The oxo-rhenium complexes [Re2O7] (1), [ReMeO 3] (2), [Re(η5-C5H5)O 3] (3), [ReO2Cl(DMSO)2] (4), [ReO 2Me(PhCCPh)] (5), and [ReOCl3(PPh3) 2] (6) catalyze the hydrosilylation of aliphatic and aromatic aldehydes with dimethylphenylsilane in C6D6 solutions. Compound 1 catalyzes the hydrosilylation of aldehydes at room temperature, affording the corresponding silyl ethers in good yield, but is ineffective as ketone hydrosilylation catalyst. The reactions of aldehydes and ketones with dimethylphenylsilane using compounds 2-6 as catalysts, require heating at 80 °C. The scope of rhenium oxides-mediated hydrosilylation with a variety of aldehydes and ketones has been studied. Methyltrioxorhenium(VII) (2) and oxotrichlorobis(triphenylphosphine)rhenium(V) (6) shown to be the most active and versatile catalysts for the hydrosilylation of aliphatic and aromatic aldehydes and also ketones. The dioxo-rhenium derivatives [ReO 2Me(PhCCPh)] and [ReO2Cl(DMSO)2] also catalyze the reaction of dimethylphenylsilane and aldehydes, although longer reaction times were required.",

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AU - Romão, Carlos C.

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N2 - The oxo-rhenium complexes [Re2O7] (1), [ReMeO 3] (2), [Re(η5-C5H5)O 3] (3), [ReO2Cl(DMSO)2] (4), [ReO 2Me(PhCCPh)] (5), and [ReOCl3(PPh3) 2] (6) catalyze the hydrosilylation of aliphatic and aromatic aldehydes with dimethylphenylsilane in C6D6 solutions. Compound 1 catalyzes the hydrosilylation of aldehydes at room temperature, affording the corresponding silyl ethers in good yield, but is ineffective as ketone hydrosilylation catalyst. The reactions of aldehydes and ketones with dimethylphenylsilane using compounds 2-6 as catalysts, require heating at 80 °C. The scope of rhenium oxides-mediated hydrosilylation with a variety of aldehydes and ketones has been studied. Methyltrioxorhenium(VII) (2) and oxotrichlorobis(triphenylphosphine)rhenium(V) (6) shown to be the most active and versatile catalysts for the hydrosilylation of aliphatic and aromatic aldehydes and also ketones. The dioxo-rhenium derivatives [ReO 2Me(PhCCPh)] and [ReO2Cl(DMSO)2] also catalyze the reaction of dimethylphenylsilane and aldehydes, although longer reaction times were required.

AB - The oxo-rhenium complexes [Re2O7] (1), [ReMeO 3] (2), [Re(η5-C5H5)O 3] (3), [ReO2Cl(DMSO)2] (4), [ReO 2Me(PhCCPh)] (5), and [ReOCl3(PPh3) 2] (6) catalyze the hydrosilylation of aliphatic and aromatic aldehydes with dimethylphenylsilane in C6D6 solutions. Compound 1 catalyzes the hydrosilylation of aldehydes at room temperature, affording the corresponding silyl ethers in good yield, but is ineffective as ketone hydrosilylation catalyst. The reactions of aldehydes and ketones with dimethylphenylsilane using compounds 2-6 as catalysts, require heating at 80 °C. The scope of rhenium oxides-mediated hydrosilylation with a variety of aldehydes and ketones has been studied. Methyltrioxorhenium(VII) (2) and oxotrichlorobis(triphenylphosphine)rhenium(V) (6) shown to be the most active and versatile catalysts for the hydrosilylation of aliphatic and aromatic aldehydes and also ketones. The dioxo-rhenium derivatives [ReO 2Me(PhCCPh)] and [ReO2Cl(DMSO)2] also catalyze the reaction of dimethylphenylsilane and aldehydes, although longer reaction times were required.

KW - Catalysis

KW - Hydrosilylation

KW - Oxo

KW - Rhenium

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JF - Journal Of Molecular Catalysis A-Chemical

SN - 1381-1169

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ER -

Reduction of carbonyl groups by high-valent rhenium oxides

Abstract

Keywords

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