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One Pot Conversion of Olefins to Carbonyl Compounds by Hydroboration / NMO-TPAP Oxidation

Matthew H. Yates*

*Department of Chemistry, Rice University, 6100 Main Street, Houston, Texas

M. H. Yates, Tetrahedron Lett., 1997, 38, 2813-2816.

DOI: 10.1016/S0040-4039(97)00476-0


Abstract

An efficient method for the oxidation of olefins to the less substituted carbonyl compounds is described. This one pot conversion includes hydroboration with borane dimethyl sulfide (BDMS) which is followed by oxidation of the resulting alkylboranes with tetrapropylammonium perruthenate (TPAP) and N-methylmorpholine N-oxide.

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Details

The document describes a new method for the one-pot conversion of olefins to carbonyl compounds using hydroboration followed by oxidation with tetrapropylammonium perruthenate (TPAP) and N-methylmorpholine N-oxide (NMO). This method, developed by Matthew H. Yates at Rice University, avoids the intermediate isolation of alcohols, making the process more efficient and environmentally friendly. The procedure involves adding borane dimethyl sulfide (BDMS) to an olefin in anhydrous ether, followed by treatment with NMO and a catalytic amount of TPAP. The reaction typically completes in about 5 minutes. The method is effective for converting olefins to both ketones and aldehydes, with yields varying based on the substrate and conditions. The document also discusses the challenges of using this method on molecules with existing carbonyl groups and provides detailed experimental procedures for different scenarios. The research was supported by grants from the National Institutes of Health, the National Science Foundation, and the Robert A. Welch Foundation. This new technique offers a mild and efficient alternative for the oxidative conversion of olefins to carbonyl compounds.


Key Words

Hydroboration, NMO, TPAP, Ketones


ID: J72-Y1997-300