Polymer-Supported IBX-Amide Reagents: Significant Role of Spacer and Additive in Alcohol Oxidation

Abstract

We found that the spacer and additive play a significant role in the oxidation of alkyl alcohols using polymer-supported IBX-amide reagents. The introduction of the spacer between the polymer support and IBX-amide group improved the initial conversion rate (up to 60% conversion). Furthermore, various alcohol compounds, when reacted with IBX-amide resin in the presence of BF₃·OEt₂, were effectively converted into the corresponding aldehydes or ketones within 5-30 minutes in high purities (>94%) at room temperature.

spacer - additive - IBX-amide resin

References

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Oxidation of 1-decanol (1 equiv) was performed using IBX-amide resin 1 (1.3 equiv) with N-methyl hexanamide (1.3 equiv) in CHCl₃ at r.t. The reaction mixture was analyzed by GC-MS after 3 h and 6 h. The conversion of 1-decanol was compared with that from the oxidation of 1-decanol without N-methyl hexanamide (NMH) under the same condition; 37% (with NMH) and 34% (without NMH) after 3 h, 43% (with NMH) and 44% (without NMH) after 6 h. No reaction between NMH and IBX-amide resin 1 was detected.

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