Selective Oxidation of Alcohols by a H2O2-RuCl3 System under Phase-Transfer Conditions

Gabriela Barak; Jihad Dakka; Yoel Sasson

doi:10.1021/jo00250a025

Selective Oxidation of Alcohols by a H₂O₂-RuCl₃ System under Phase-Transfer Conditions

Gabriela Barak, Jihad Dakka, Yoel Sasson^*

^*Corresponding author for this work

Institute of Chemistry

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

114 Scopus citations

Abstract

The selective oxidation of primary aliphatic alcohols to carboxylic acids (60-70% selectivity), secondary alcohols to ketones (100% selectivity), and primary benzylic alcohols to aldehydes (95-100% selectivity) or carboxylic acids as well as the selective oxidation of allylic alcohol to ketones (80% selectivity) was performed in a H₂O₂-RuCl₃-3H₂O phase transfer catalyst (PTC) system at a high substrate:RuCl₃ (625:1) ratio. It has also been found that the PTC not only has a role in the extraction of RuC1₃ and H₂O₂ in the organic phase but also protects the metallic catalyst against reduction. Other metallic catalysts as PdCl₂, RhCl₃-3H₂O, MnCl₂4H₂O, and CoCl-6H₂O show poor conversion and selectivity.

Original language	English
Pages (from-to)	3553-3555
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	53
Issue number	15
DOIs	https://doi.org/10.1021/jo00250a025
State	Published - 1 Feb 1988

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title = "Selective Oxidation of Alcohols by a H2O2-RuCl3 System under Phase-Transfer Conditions",

abstract = "The selective oxidation of primary aliphatic alcohols to carboxylic acids (60-70% selectivity), secondary alcohols to ketones (100% selectivity), and primary benzylic alcohols to aldehydes (95-100% selectivity) or carboxylic acids as well as the selective oxidation of allylic alcohol to ketones (80% selectivity) was performed in a H2O2-RuCl3-3H2O phase transfer catalyst (PTC) system at a high substrate:RuCl3 (625:1) ratio. It has also been found that the PTC not only has a role in the extraction of RuC13 and H2O2 in the organic phase but also protects the metallic catalyst against reduction. Other metallic catalysts as PdCl2, RhCl3-3H2O, MnCl24H2O, and CoCl-6H2O show poor conversion and selectivity.",

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T1 - Selective Oxidation of Alcohols by a H2O2-RuCl3 System under Phase-Transfer Conditions

AU - Barak, Gabriela

AU - Dakka, Jihad

AU - Sasson, Yoel

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N2 - The selective oxidation of primary aliphatic alcohols to carboxylic acids (60-70% selectivity), secondary alcohols to ketones (100% selectivity), and primary benzylic alcohols to aldehydes (95-100% selectivity) or carboxylic acids as well as the selective oxidation of allylic alcohol to ketones (80% selectivity) was performed in a H2O2-RuCl3-3H2O phase transfer catalyst (PTC) system at a high substrate:RuCl3 (625:1) ratio. It has also been found that the PTC not only has a role in the extraction of RuC13 and H2O2 in the organic phase but also protects the metallic catalyst against reduction. Other metallic catalysts as PdCl2, RhCl3-3H2O, MnCl24H2O, and CoCl-6H2O show poor conversion and selectivity.

AB - The selective oxidation of primary aliphatic alcohols to carboxylic acids (60-70% selectivity), secondary alcohols to ketones (100% selectivity), and primary benzylic alcohols to aldehydes (95-100% selectivity) or carboxylic acids as well as the selective oxidation of allylic alcohol to ketones (80% selectivity) was performed in a H2O2-RuCl3-3H2O phase transfer catalyst (PTC) system at a high substrate:RuCl3 (625:1) ratio. It has also been found that the PTC not only has a role in the extraction of RuC13 and H2O2 in the organic phase but also protects the metallic catalyst against reduction. Other metallic catalysts as PdCl2, RhCl3-3H2O, MnCl24H2O, and CoCl-6H2O show poor conversion and selectivity.

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Selective Oxidation of Alcohols by a H₂O₂-RuCl₃ System under Phase-Transfer Conditions

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